433 lines
42 KiB
XML
433 lines
42 KiB
XML
<document id="823F9E65F3A43B4C70509D7EE1EFA432" ID-CLB-Dataset="285216" ID-DOI="10.1016/j.phytochem.2015.11.002" ID-GBIF-Dataset="18ecad6c-abce-4590-9b84-edd0e9b30119" ID-ISSN="1873-3700" ID-PMC="PMC4724521" ID-PubMed="26626160" ID-Zenodo-Dep="10485359" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="julia" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="julia" IM.taxonomicNames_approvedBy="julia" IM.treatments_approvedBy="julia" checkinTime="1704944474214" checkinUser="felipe" docAuthor="Sun, Pengfei, Leeson, Cristian, Zhi, Xiaoduo, Leng, Fenfei, Pierce, Richard H., Henry, Michael S. & Rein, Kathleen S." docDate="2016" docId="03ABA26DFF9DA9626505FC78FED8FAAB" docLanguage="en" docName="Phytochemistry.122.11-21.pdf" docOrigin="Phytochemistry 122" docSource="http://dx.doi.org/10.1016/j.phytochem.2015.11.002" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Karenia brevis EH" docType="treatment" docVersion="7" lastPageNumber="16" masterDocId="FF92DA15FF99A9676577FFBBFF92FF81" masterDocTitle="Characterization of an epoxide hydrolase from the Florida red tide dinoflagellate, Karenia brevis" masterLastPageNumber="21" masterPageNumber="11" pageNumber="15" updateTime="1705665227329" updateUser="julia">
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<mods:mods id="B3E4517FD80B7A7E8FEFB21EE7677275" xmlns:mods="http://www.loc.gov/mods/v3">
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<mods:titleInfo id="44E08A5E2D46759FF3BD75714C36F2CE">
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<mods:title id="467CAFA6FE0190AE91E1DBA3B8912840">Characterization of an epoxide hydrolase from the Florida red tide dinoflagellate, Karenia brevis</mods:title>
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<mods:name id="6AA6AC6243E4054D02335A4B63E99C23" type="personal">
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<mods:roleTerm id="C6DA902A5C759DEA30153E23CDFE06F9">Author</mods:roleTerm>
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<mods:namePart id="D3897B93F80458392422DCF059CE7EE7">Sun, Pengfei</mods:namePart>
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<mods:affiliation id="B3CA8E4264EE75CB408346615B998270">Department of Chemistry and Biochemistry, Florida International University, Miami, FL 33199, USA</mods:affiliation>
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</mods:name>
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<mods:roleTerm id="25E586B9C348DFE6C4D7AF00778BB2F6">Author</mods:roleTerm>
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<mods:namePart id="43D6276D612FFE001CE54158F4D5EA84">Leeson, Cristian</mods:namePart>
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<mods:roleTerm id="0B6148E40CB1F714C47DDD4DB98D4937">Author</mods:roleTerm>
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<mods:namePart id="3EE70E178AAEC4EA676AD3F650863664">Zhi, Xiaoduo</mods:namePart>
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</mods:name>
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<mods:name id="43850003DAF1D6496FF0591EADCA092E" type="personal">
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<mods:roleTerm id="38666C216B9D15E9EF7C6BEF3C1F04CB">Author</mods:roleTerm>
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</mods:role>
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<mods:namePart id="735A56261CAF05436E027FBE5E659A4D">Leng, Fenfei</mods:namePart>
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<mods:roleTerm id="7504296A9249030B3A5614E9249AEE87">Author</mods:roleTerm>
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<mods:namePart id="5721191E5653F07B3CED9B76BFBFF54B">Pierce, Richard H.</mods:namePart>
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<mods:namePart id="16153B0C8E3896B4002E3CB63338FED3">Henry, Michael S.</mods:namePart>
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<mods:namePart id="3145EC6DBF2153BB05FBAE6C098A4961">Rein, Kathleen S.</mods:namePart>
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<mods:title id="2F4C691B0D934100E230F46B234B9A0B">Phytochemistry</mods:title>
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<mods:part id="D84454449F8FE04C060C538DCB28EB44">
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<mods:date id="5EFEC18B8013E8C77BED51A39EE41A25">2016</mods:date>
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<mods:number id="DDA07434C67A2C9532C3DBF1F7AC1523">2016-02-29</mods:number>
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<mods:number id="A614D1110AF3DCDE1649856F1947F2D1">122</mods:number>
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<mods:classification id="623CF8FFBC182AE3DCFCF1EB05A7D690">journal article</mods:classification>
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<mods:identifier id="2C3484931CA295BB643BF5E39FE024A4" type="CLB-Dataset">285216</mods:identifier>
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<mods:identifier id="CDED811A4445C967DF346ABC1F185580" type="DOI">10.1016/j.phytochem.2015.11.002</mods:identifier>
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<mods:identifier id="C8D9051B8BDD449D4269E03F50520082" type="GBIF-Dataset">18ecad6c-abce-4590-9b84-edd0e9b30119</mods:identifier>
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<treatment id="03ABA26DFF9DA9626505FC78FED8FAAB" ID-DOI="http://doi.org/10.5281/zenodo.10514327" ID-GBIF-Taxon="220760399" ID-Zenodo-Dep="10514327" LSID="urn:lsid:plazi:treatment:03ABA26DFF9DA9626505FC78FED8FAAB" httpUri="http://treatment.plazi.org/id/03ABA26DFF9DA9626505FC78FED8FAAB" lastPageId="5" lastPageNumber="16" pageId="4" pageNumber="15">
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<subSubSection id="C31840F0FF9DA9636505FC78FE5CFC56" box="[114,462,963,983]" pageId="4" pageNumber="15" type="nomenclature">
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<paragraph id="8BBD137BFF9DA9636505FC78FE5CFC56" blockId="4.[114,462,963,983]" box="[114,462,963,983]" pageId="4" pageNumber="15">
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<heading id="D0F5A417FF9DA9636505FC78FE5CFC56" box="[114,462,963,983]" fontSize="36" level="2" pageId="4" pageNumber="15" reason="3">
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<emphasis id="B976CF69FF9DA9636505FC78FE5CFC56" box="[114,462,963,983]" italics="true" pageId="4" pageNumber="15">
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2.3. Characterization of
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<taxonomicName id="4C0268F8FF9DA963642EFC78FE3EFC56" authority="EH" authorityName="EH" box="[345,428,963,983]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">K. brevis</taxonomicName>
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EH
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="C31840F0FF9DA96265E6FC47FED8FAAB" lastPageId="5" lastPageNumber="16" pageId="4" pageNumber="15" type="description">
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<paragraph id="8BBD137BFF9DA96365E6FC47FA4CFEF0" blockId="4.[113,784,1020,1123]" lastBlockId="4.[831,1502,181,1122]" pageId="4" pageNumber="15">
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Fluorescent probe sets
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<emphasis id="B976CF69FF9DA96364F5FC47FE0FFB8E" bold="true" box="[386,413,1020,1039]" pageId="4" pageNumber="15">3b</emphasis>
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/
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<emphasis id="B976CF69FF9DA96364D3FC47FE2DFB8E" bold="true" box="[420,447,1020,1039]" pageId="4" pageNumber="15">5b</emphasis>
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and
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<emphasis id="B976CF69FF9DA9636480FC47FD82FB8E" bold="true" box="[503,528,1020,1039]" pageId="4" pageNumber="15">3a</emphasis>
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/
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<emphasis id="B976CF69FF9DA9636760FC47FDA3FB8E" bold="true" box="[535,561,1020,1039]" pageId="4" pageNumber="15">5a</emphasis>
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were used for initial characterization of the expressed
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<taxonomicName id="4C0268F8FF9DA96364AFFBACFDBCFBAA" authority="EH" authorityName="EH" box="[472,558,1047,1067]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
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<emphasis id="B976CF69FF9DA96364AFFBACFDBCFBAA" box="[472,558,1047,1067]" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
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</taxonomicName>
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EH (
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<figureCitation id="13390FFEFF9DA963671EFBA3FD3CFBAA" box="[617,686,1048,1067]" captionStart="Fig" captionStartId="4.[113,139,1953,1967]" captionTargetBox="[204,1382,1176,1924]" captionTargetPageId="4" captionText="Fig. 3. (A) Alignment of putative K.brevis EH1 with Aspergillus niger EH.Catalytic residues are indicated by.. (B) SDS PAGE of expressed protein after purification and dialysis. Lanes M: Precision Plus Protein Unstained Standards (Biorad 161-0363) lane 1: lysate; lanes 2–3: column flow-through; lanes 4–5: column washes; lane 6: elution.C.EH (5b) and esterase (3b) assay of purified K. brevis EH." figureDoi="http://doi.org/10.5281/zenodo.10485363" httpUri="https://zenodo.org/record/10485363/files/figure.png" pageId="4" pageNumber="15">Fig. 3C</figureCitation>
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). The EH was optimally active at pH 6.8–7.1, with half-maximal activity at pH 6.5 and 8.3. Consistent with the selectivity observed in the
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<taxonomicName id="4C0268F8FF9DA963678AFBF4FCEAFF48" authority="CFE" authorityName="CFE" box="[765,888,181,1123]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
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<emphasis id="B976CF69FF9DA963678AFBF4FCEAFF48" box="[765,888,181,1123]" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
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</taxonomicName>
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CFE, the purified EH showed a preference for epoxide
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<emphasis id="B976CF69FF9DA96360E6FF0DFA39FF48" bold="true" box="[1425,1451,182,201]" pageId="4" pageNumber="15">5b</emphasis>
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over
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<emphasis id="B976CF69FF9DA9636648FF69FCCAFF64" bold="true" box="[831,856,210,229]" pageId="4" pageNumber="15">5a</emphasis>
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. The ratio of initial rates (
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<emphasis id="B976CF69FF9DA963612FFF6AFBF7FF64" box="[1112,1125,209,229]" italics="true" pageId="4" pageNumber="15">V</emphasis>
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<subScript id="1786113EFF9DA9636112FF60FBFCFF66" attach="left" box="[1125,1134,219,231]" fontSize="5" pageId="4" pageNumber="15">o</subScript>
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) for substrates
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<emphasis id="B976CF69FF9DA963607DFF69FAB1FF64" bold="true" box="[1290,1315,210,229]" pageId="4" pageNumber="15">5a</emphasis>
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:
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<emphasis id="B976CF69FF9DA963605DFF69FAD6FF64" bold="true" box="[1322,1348,210,229]" pageId="4" pageNumber="15">5b</emphasis>
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was 1:4. Epoxide hydrolases of the a,b- hydrolase
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<typeStatus id="54B9ADD9FF9DA96361DFFF55FB47FE80" box="[1192,1237,238,257]" pageId="4" pageNumber="15">type</typeStatus>
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share significant homologies with other hydrolases, including esterases. As done with the CFE, EH activity was distinguished from esterase activity using the substrates
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<emphasis id="B976CF69FF9DA96366A5FEF9FC79FED4" bold="true" box="[978,1003,322,341]" pageId="4" pageNumber="15">3a</emphasis>
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and
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<emphasis id="B976CF69FF9DA963616CFEF9FBA6FED4" bold="true" box="[1051,1076,322,341]" pageId="4" pageNumber="15">5a</emphasis>
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. No activity was observed using the esterase probes indicating that the expressed protein was indeed an EH.
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</paragraph>
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<paragraph id="8BBD137BFF9DA9636629FEC2FC1EFCE6" blockId="4.[831,1502,181,1122]" pageId="4" pageNumber="15">
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Substrate and enantioselectivity of the
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<taxonomicName id="4C0268F8FF9DA9636195FEC3FAA1FE0D" authority="EH" authorityName="EH" box="[1250,1331,376,396]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
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<emphasis id="B976CF69FF9DA9636195FEC3FAA1FE0D" box="[1250,1331,376,396]" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
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</taxonomicName>
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EH was assessed by kinetic studies. Kinetic parameters of the enzyme using substrates
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<emphasis id="B976CF69FF9DA96366FDFE0AFC31FE45" bold="true" box="[906,931,433,452]" pageId="4" pageNumber="15">5a</emphasis>
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and
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<emphasis id="B976CF69FF9DA96366AFFE0AFC60FE45" bold="true" box="[984,1010,433,452]" pageId="4" pageNumber="15">5b</emphasis>
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were performed using the sensitive fluorescent assay. Other substrates having no fluorescent reporter group were evaluated by GC–MS analysis of the reaction mixtures using 1- naphthol as an internal standard. The data shown in
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<tableCitation id="C68026C0FF9DA963602CFDBEFA37FD99" box="[1371,1445,517,536]" captionStart="Table 1" captionStartId="5.[87,131,183,197]" captionTargetPageId="5" captionText="Table 1 Kinetic parameters of the K. brevis EH with various substrates and inhibitors." httpUri="http://table.plazi.org/id/DF7D43F3FF9CA9626520FF0CFD2FFF5D" pageId="4" pageNumber="15" tableUuid="DF7D43F3FF9CA9626520FF0CFD2FFF5D">Table 1</tableCitation>
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indicates that the
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<taxonomicName id="4C0268F8FF9DA96366AEFD9BFBBDFDB5" authority="EH" authorityName="EH" box="[985,1071,544,564]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
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<emphasis id="B976CF69FF9DA96366AEFD9BFBBDFDB5" box="[985,1071,544,564]" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
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</taxonomicName>
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EH has a strong preference for terminal epoxides over internal epoxides (Entries 3–9 vs. Entries 1–2). Aliphatic substituents are preferred over aromatic substituents by approximately 5:1 (Entries 7–9 vs. Entries 3–6) and the enzyme shows only a slight preference for
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<emphasis id="B976CF69FF9DA96361DEFD34FB24FD22" box="[1193,1206,655,675]" italics="true" pageId="4" pageNumber="15">R</emphasis>
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over
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<emphasis id="B976CF69FF9DA9636183FD34FB6DFD22" box="[1268,1279,655,675]" italics="true" pageId="4" pageNumber="15">S</emphasis>
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enantiomers (Entries 3 and 4). The reaction rates using 1,2-disubstituted epoxides as substrates are too slow to be determined using the GC–MS method. However, disubstituted epoxides proved to be inhibitors of the
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<taxonomicName id="4C0268F8FF9DA96360BDFD58FCEAFC92" authority="EH" authorityName="EH" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
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<emphasis id="B976CF69FF9DA96360BDFD58FCEAFC92" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
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</taxonomicName>
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EH only when an aromatic substituent is present (Entries 10–12 vs. Entries 13–14) and
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<emphasis id="B976CF69FF9DA9636106FCA0FB18FCAE" box="[1137,1162,795,815]" italics="true" pageId="4" pageNumber="15">cis</emphasis>
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-disubstituted epoxides are more potent inhibitors than those that are
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<emphasis id="B976CF69FF9DA96361B2FC8CFB64FCCA" box="[1221,1270,823,843]" italics="true" pageId="4" pageNumber="15">trans</emphasis>
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-disubstituted (Entries 10–12).
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</paragraph>
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<paragraph id="8BBD137BFF9DA9626629FCCBFDA3FB92" blockId="4.[831,1502,181,1122]" lastBlockId="5.[87,757,857,1322]" lastPageId="5" lastPageNumber="16" pageId="4" pageNumber="15">
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A noteworthy distinction between the monensin (
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<emphasis id="B976CF69FF9DA9636010FCCBFAE6FC02" bold="true" box="[1383,1396,880,899]" pageId="4" pageNumber="15">2</emphasis>
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) pathway and the proposed brevetoxin (
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<emphasis id="B976CF69FF9DA963611BFC30FBEBFC1F" bold="true" box="[1132,1145,907,926]" pageId="4" pageNumber="15">1</emphasis>
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) pathway is the site of nucleophilic attack on the epoxide substrate (
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<figureCitation id="13390FFEFF9DA96361FFFC1CFB7AFC3A" box="[1160,1256,935,955]" captionStart="Scheme 1" captionStartId="1.[417,482,975,989]" captionTargetBox="[133,1418,183,945]" captionTargetId="figure-646@1.[133,1419,181,946]" captionTargetPageId="1" captionText="Scheme 1. Proposed polyether ladder (left) and confirmed polyether (right) biosynthesis." figureDoi="http://doi.org/10.5281/zenodo.10514927" httpUri="https://zenodo.org/record/10514927/files/figure.png" pageId="4" pageNumber="15">Scheme 1</figureCitation>
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). In the case of non-ladder polyethers, the majority of epoxide ring opening reactions proceed via attack at the proximal carbon (
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<emphasis id="B976CF69FF9DA96361ABFC65FA8DFC73" box="[1244,1311,990,1010]" italics="true" pageId="4" pageNumber="15">exo-tet</emphasis>
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cyclization) while polyether ladder formation requires attack at the distal carbon (
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<emphasis id="B976CF69FF9DA9636630FBADFC0AFBAB" box="[839,920,1046,1066]" italics="true" pageId="4" pageNumber="15">endo-tet</emphasis>
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cyclization). Both the empirical Baldwin’s rules (
|
||
<bibRefCitation id="EF936E8AFF9DA9636630FB88FC4BFBC7" author="Baldwin, J. E." box="[839,985,1075,1094]" pageId="4" pageNumber="15" pagination="734 - 736" refId="ref10203" refString="Baldwin, J. E., 1976. Rules for ring closure. J. Chem. Soc. Chem. Commun., 734 - 736" type="book chapter" year="1976">Baldwin, 1976</bibRefCitation>
|
||
) and molecular orbital calculations (
|
||
<bibRefCitation id="EF936E8AFF9DA9636021FB88FCE0FBE3" author="Gruber, K. & Zhou, B. & Houk, K. N. & Lerner, R. A. & Shevlin, C. G. & Wilson, I. A." pageId="4" pageNumber="15" pagination="7062 - 7074" refId="ref10903" refString="Gruber, K., Zhou, B., Houk, K. N., Lerner, R. A., Shevlin, C. G., Wilson, I. A., 1999. Structural basis for antibody catalysis of a disfavored ring closure reaction. Biochemistry 38, 7062 - 7074." type="journal article" year="1999">Gruber et al., 1999</bibRefCitation>
|
||
) indicate that the
|
||
<emphasis id="B976CF69FF9DA9636146FBF5FB10FBE3" box="[1073,1154,1102,1122]" italics="true" pageId="4" pageNumber="15">endo-tet</emphasis>
|
||
cyclization pathway is kinetically disfavored. The exception among the bacterial polyketides is lasalocid. In this polyether, the pyran ring arises from the
|
||
<emphasis id="B976CF69FF9CA96267D4FCCFFD66FC09" box="[675,756,884,904]" italics="true" pageId="5" pageNumber="16">endo-tet</emphasis>
|
||
cyclization of an intermediate epoxide. This reaction is catalyzed by the EH Lsd19. Lsd19 is a bifunctional enzyme consisting of two domains (A and B). Each domain is responsible for the cyclization of one of the rings with Lsd19B catalyzing the
|
||
<emphasis id="B976CF69FF9CA9626726FC58FD30FC76" box="[593,674,995,1015]" italics="true" pageId="5" pageNumber="16">endo-tet</emphasis>
|
||
cyclization of the terminal ring (
|
||
<bibRefCitation id="EF936E8AFF9CA9626429FBBBFDB6FB92" author="Minami, A. & Migita, A. & Inada, D. & Hotta, K. & Watanabe, K. & Oguri, H. & Oikawa, H." box="[350,548,1024,1043]" pageId="5" pageNumber="16" pagination="1638 - 1641" refId="ref11413" refString="Minami, A., Migita, A., Inada, D., Hotta, K., Watanabe, K., Oguri, H., Oikawa, H., 2011. Enzymatic epoxide-opening cascades catalyzed by a pair of epoxide hydrolases in the ionophore polyether biosynthesis. Org. Lett. 13, 1638 - 1641." type="journal article" year="2011">Minami et al., 2011</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<caption id="DF7D43F3FF9DA9636506F81AFE66F85C" ID-DOI="http://doi.org/10.5281/zenodo.10485363" ID-Zenodo-Dep="10485363" httpUri="https://zenodo.org/record/10485363/files/figure.png" pageId="4" pageNumber="15" startId="4.[113,139,1953,1967]" targetBox="[204,1382,1176,1924]" targetPageId="4" targetType="figure">
|
||
<paragraph id="8BBD137BFF9DA9636506F81AFE66F85C" blockId="4.[113,1502,1953,2013]" pageId="4" pageNumber="15">
|
||
<emphasis id="B976CF69FF9DA9636506F81AFF30F82E" bold="true" box="[113,162,1953,1967]" pageId="4" pageNumber="15">Fig. 3.</emphasis>
|
||
(A) Alignment of putative
|
||
<taxonomicName id="4C0268F8FF9DA963640EF81AFE4BF82E" authority="EH" authorityName="EH" box="[377,473,1953,1968]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
|
||
<emphasis id="B976CF69FF9DA963640EF81AFE28F831" box="[377,442,1953,1968]" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
|
||
EH
|
||
</taxonomicName>
|
||
1 with
|
||
<taxonomicName id="4C0268F8FF9DA963677BF81AFD61F82E" authority="EH. Catalytic" authorityName="EH. Catalytic" box="[524,755,1953,1968]" class="Sordariomycetes" family="Microascaceae" genus="Aspergillus" kingdom="Fungi" order="Microascales" pageId="4" pageNumber="15" phylum="Ascomycota" rank="species" species="niger">
|
||
<emphasis id="B976CF69FF9DA963677BF81AFD18F831" box="[524,650,1953,1968]" italics="true" pageId="4" pageNumber="15">Aspergillus niger</emphasis>
|
||
EH. Catalytic
|
||
</taxonomicName>
|
||
residues are indicated by .. (B) SDS PAGE of expressed protein after purification and dialysis. Lanes
|
||
<emphasis id="B976CF69FF9DA96365D4F803FF21F847" bold="true" box="[163,179,1976,1990]" pageId="4" pageNumber="15">M</emphasis>
|
||
: Precision Plus Protein Unstained Standards (Biorad 161-0363) lane 1: lysate; lanes 2–3: column flow-through; lanes 4–5: column washes; lane 6: elution. C. EH (
|
||
<emphasis id="B976CF69FF9DA96360B6F803FA44F847" bold="true" box="[1473,1494,1976,1990]" pageId="4" pageNumber="15">5b</emphasis>
|
||
) and esterase (
|
||
<emphasis id="B976CF69FF9DA9636594F874FF6AF85C" bold="true" box="[227,248,1999,2013]" pageId="4" pageNumber="15">3b</emphasis>
|
||
) assay of purified
|
||
<taxonomicName id="4C0268F8FF9DA96364E7F875FE66F85C" authority="EH." authorityName="EH." box="[400,500,1998,2013]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="4" pageNumber="15" phylum="Arthropoda" rank="species" species="brevis">
|
||
<emphasis id="B976CF69FF9DA96364E7F875FE40F85C" box="[400,466,1998,2013]" italics="true" pageId="4" pageNumber="15">K. brevis</emphasis>
|
||
EH.
|
||
</taxonomicName>
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="DF7D43F3FF9CA9626520FF0CFD2FFF5D" ID-Table-UUID="DF7D43F3FF9CA9626520FF0CFD2FFF5D" httpUri="http://table.plazi.org/id/DF7D43F3FF9CA9626520FF0CFD2FFF5D" pageId="5" pageNumber="16" startId="5.[87,131,183,197]" targetBox="[110,1451,239,589]" targetIsTable="true" targetPageId="5" targetType="table">
|
||
<paragraph id="8BBD137BFF9CA9626520FF0CFF01FF44" blockId="5.[87,701,183,220]" box="[87,147,183,197]" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA9626520FF0CFF01FF44" bold="true" box="[87,147,183,197]" pageId="5" pageNumber="16">Table 1</emphasis>
|
||
</paragraph>
|
||
<paragraph id="8BBD137BFF9CA9626520FF75FD2FFF5D" blockId="5.[87,701,183,220]" box="[87,701,205,220]" pageId="5" pageNumber="16">
|
||
Kinetic parameters of the
|
||
<taxonomicName id="4C0268F8FF9CA9626450FF76FE11FF5D" authority="EH" authorityName="EH" box="[295,387,205,220]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="5" pageNumber="16" phylum="Arthropoda" rank="species" species="brevis">
|
||
<emphasis id="B976CF69FF9CA9626450FF76FEFAFF5D" box="[295,360,205,220]" italics="true" pageId="5" pageNumber="16">K. brevis</emphasis>
|
||
EH
|
||
</taxonomicName>
|
||
with various substrates and inhibitors.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BBD137BFF9CA9626519FF4FFAF1FDCC" pageId="5" pageNumber="16">
|
||
<table id="F902E1DBFF9C56986519FF54FA39FDCC" box="[110,1451,239,589]" gridcols="6" gridrows="15" pageId="5" pageNumber="16">
|
||
<tr id="35321139FF9C56986519FF54FA39FE85" box="[110,1451,239,260]" gridrow="0" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FF54FF08FE85" box="[110,154,239,260]" gridcol="0" gridrow="0" pageId="5" pageNumber="16">Entry</th>
|
||
<th id="76E37845FF9C56986453FF54FD8CFE85" box="[292,542,239,260]" gridcol="1" gridrow="0" pageId="5" pageNumber="16">Substrate</th>
|
||
<th id="76E37845FF9C569867DFFF54FD7FFE85" box="[680,749,239,260]" gridcol="2" gridrow="0" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA96267DFFF48FD21FE83" box="[680,691,243,258]" italics="true" pageId="5" pageNumber="16">K</emphasis>
|
||
m (LM)
|
||
</th>
|
||
<th id="76E37845FF9C5698660FFF54FC2CFE85" box="[888,958,239,260]" gridcol="3" gridrow="0" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA962660FFF48FC13FE83" box="[888,897,243,258]" italics="true" pageId="5" pageNumber="16">k</emphasis>
|
||
(s –1) cat
|
||
</th>
|
||
<th id="76E37845FF9C5698613EFF54FB5DFE85" box="[1097,1231,239,260]" gridcol="4" gridrow="0" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA962613EFF48FBC0FE83" box="[1097,1106,243,258]" italics="true" pageId="5" pageNumber="16">k</emphasis>
|
||
(s –1)/
|
||
<emphasis id="B976CF69FF9CA96261E2FF48FB32FE83" box="[1173,1184,243,258]" italics="true" pageId="5" pageNumber="16">K</emphasis>
|
||
(M) cat m
|
||
</th>
|
||
<th id="76E37845FF9C5698602EFF54FA39FE85" box="[1369,1451,239,260]" gridcol="5" gridrow="0" pageId="5" pageNumber="16">IC50 (mM)</th>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FEAEFA39FEA5" box="[110,1451,277,292]" gridrow="1" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FEAEFF08FEA5" box="[110,154,277,292]" gridcol="0" gridrow="1" pageId="5" pageNumber="16">1</th>
|
||
<td id="76E37845FF9C56986453FEAEFD8CFEA5" box="[292,542,277,292]" gridcol="1" gridrow="1" pageId="5" pageNumber="16">
|
||
Probe
|
||
<emphasis id="B976CF69FF9CA962642FFEADFEFEFEA5" bold="true" box="[344,364,278,292]" pageId="5" pageNumber="16">5a</emphasis>
|
||
(R = Ph)
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFEAEFD7FFEA5" box="[680,749,277,292]" gridcol="2" gridrow="1" pageId="5" pageNumber="16">13.6</td>
|
||
<td id="76E37845FF9C5698660FFEAEFC2CFEA5" box="[888,958,277,292]" gridcol="3" gridrow="1" pageId="5" pageNumber="16">7.81E–4</td>
|
||
<td id="76E37845FF9C5698613EFEAEFB5DFEA5" box="[1097,1231,277,292]" gridcol="4" gridrow="1" pageId="5" pageNumber="16">57.4</td>
|
||
<td id="76E37845FF9C5698602EFEAEFA39FEA5" box="[1369,1451,277,292]" gridcol="5" gridrow="1" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE97FA39FEBA" box="[110,1451,300,315]" gridrow="2" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE97FF08FEBA" box="[110,154,300,315]" gridcol="0" gridrow="2" pageId="5" pageNumber="16">2</th>
|
||
<td id="76E37845FF9C56986453FE97FD8CFEBA" box="[292,542,300,315]" gridcol="1" gridrow="2" pageId="5" pageNumber="16">
|
||
Probe
|
||
<emphasis id="B976CF69FF9CA962642FFE97FEFFFEBB" bold="true" box="[344,365,300,314]" pageId="5" pageNumber="16">5b</emphasis>
|
||
(R = Et)
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFE97FD7FFEBA" box="[680,749,300,315]" gridcol="2" gridrow="2" pageId="5" pageNumber="16">161</td>
|
||
<td id="76E37845FF9C5698660FFE97FC2CFEBA" box="[888,958,300,315]" gridcol="3" gridrow="2" pageId="5" pageNumber="16">4.46E–3</td>
|
||
<td id="76E37845FF9C5698613EFE97FB5DFEBA" box="[1097,1231,300,315]" gridcol="4" gridrow="2" pageId="5" pageNumber="16">27.7</td>
|
||
<td id="76E37845FF9C5698602EFE97FA39FEBA" box="[1369,1451,300,315]" gridcol="5" gridrow="2" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FEF9FA39FED3" box="[110,1451,322,338]" gridrow="3" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FEF9FF08FED3" box="[110,154,322,338]" gridcol="0" gridrow="3" pageId="5" pageNumber="16">3</th>
|
||
<td id="76E37845FF9C56986453FEF9FD8CFED3" box="[292,542,322,338]" gridcol="1" gridrow="3" pageId="5" pageNumber="16">
|
||
(
|
||
<emphasis id="B976CF69FF9CA962645CFEF9FEA7FED0" box="[299,309,322,337]" italics="true" pageId="5" pageNumber="16">R</emphasis>
|
||
) styrene oxide
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFEF9FD7FFED3" box="[680,749,322,338]" gridcol="2" gridrow="3" pageId="5" pageNumber="16">6240</td>
|
||
<td id="76E37845FF9C5698660FFEF9FC2CFED3" box="[888,958,322,338]" gridcol="3" gridrow="3" pageId="5" pageNumber="16">9.01E–1</td>
|
||
<td id="76E37845FF9C5698613EFEF9FB5DFED3" box="[1097,1231,322,338]" gridcol="4" gridrow="3" pageId="5" pageNumber="16">144</td>
|
||
<td id="76E37845FF9C5698602EFEF9FA39FED3" box="[1369,1451,322,338]" gridcol="5" gridrow="3" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FEE3FA39FEE9" box="[110,1451,344,360]" gridrow="4" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FEE3FF08FEE9" box="[110,154,344,360]" gridcol="0" gridrow="4" pageId="5" pageNumber="16">4</th>
|
||
<td id="76E37845FF9C56986453FEE3FD8CFEE9" box="[292,542,344,360]" gridcol="1" gridrow="4" pageId="5" pageNumber="16">
|
||
(
|
||
<emphasis id="B976CF69FF9CA962645CFEE3FEA1FEE9" box="[299,307,344,360]" italics="true" pageId="5" pageNumber="16">S</emphasis>
|
||
) styrene oxide
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFEE3FD7FFEE9" box="[680,749,344,360]" gridcol="2" gridrow="4" pageId="5" pageNumber="16">6430</td>
|
||
<td id="76E37845FF9C5698660FFEE3FC2CFEE9" box="[888,958,344,360]" gridcol="3" gridrow="4" pageId="5" pageNumber="16">8.32E–1</td>
|
||
<td id="76E37845FF9C5698613EFEE3FB5DFEE9" box="[1097,1231,344,360]" gridcol="4" gridrow="4" pageId="5" pageNumber="16">129</td>
|
||
<td id="76E37845FF9C5698602EFEE3FA39FEE9" box="[1369,1451,344,360]" gridcol="5" gridrow="4" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FED4FA39FEFE" box="[110,1451,367,383]" gridrow="5" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FED4FF08FEFE" box="[110,154,367,383]" gridcol="0" gridrow="5" pageId="5" pageNumber="16">5</th>
|
||
<td id="76E37845FF9C56986453FED4FD8CFEFE" box="[292,542,367,383]" gridcol="1" gridrow="5" pageId="5" pageNumber="16">
|
||
(
|
||
<emphasis id="B976CF69FF9CA962645CFED4FED1FEFE" box="[299,323,367,383]" italics="true" pageId="5" pageNumber="16">R/S</emphasis>
|
||
) styrene oxide
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFED4FD7FFEFE" box="[680,749,367,383]" gridcol="2" gridrow="5" pageId="5" pageNumber="16">6570</td>
|
||
<td id="76E37845FF9C5698660FFED4FC2CFEFE" box="[888,958,367,383]" gridcol="3" gridrow="5" pageId="5" pageNumber="16">8.58E–1</td>
|
||
<td id="76E37845FF9C5698613EFED4FB5DFEFE" box="[1097,1231,367,383]" gridcol="4" gridrow="5" pageId="5" pageNumber="16">131</td>
|
||
<td id="76E37845FF9C5698602EFED4FA39FEFE" box="[1369,1451,367,383]" gridcol="5" gridrow="5" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE3FFA39FE16" box="[110,1451,388,407]" gridrow="6" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE3FFF08FE16" box="[110,154,388,407]" gridcol="0" gridrow="6" pageId="5" pageNumber="16">6</th>
|
||
<td id="76E37845FF9C56986453FE3FFD8CFE16" box="[292,542,388,407]" gridcol="1" gridrow="6" pageId="5" pageNumber="16">a- Methylstyrene oxide</td>
|
||
<td id="76E37845FF9C569867DFFE3FFD7FFE16" box="[680,749,388,407]" gridcol="2" gridrow="6" pageId="5" pageNumber="16">5310</td>
|
||
<td id="76E37845FF9C5698660FFE3FFC2CFE16" box="[888,958,388,407]" gridcol="3" gridrow="6" pageId="5" pageNumber="16">3.31E–1</td>
|
||
<td id="76E37845FF9C5698613EFE3FFB5DFE16" box="[1097,1231,388,407]" gridcol="4" gridrow="6" pageId="5" pageNumber="16">62.3</td>
|
||
<td id="76E37845FF9C5698602EFE3FFA39FE16" box="[1369,1451,388,407]" gridcol="5" gridrow="6" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE25FA39FE2C" box="[110,1451,414,429]" gridrow="7" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE25FF08FE2C" box="[110,154,414,429]" gridcol="0" gridrow="7" pageId="5" pageNumber="16">7</th>
|
||
<td id="76E37845FF9C56986453FE25FD8CFE2C" box="[292,542,414,429]" gridcol="1" gridrow="7" pageId="5" pageNumber="16">
|
||
(
|
||
<emphasis id="B976CF69FF9CA962645CFE25FEA7FE2C" box="[299,309,414,429]" italics="true" pageId="5" pageNumber="16">R</emphasis>
|
||
) 1-butane oxide
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFE25FD7FFE2C" box="[680,749,414,429]" gridcol="2" gridrow="7" pageId="5" pageNumber="16">25,800</td>
|
||
<td id="76E37845FF9C5698660FFE25FC2CFE2C" box="[888,958,414,429]" gridcol="3" gridrow="7" pageId="5" pageNumber="16">6.15</td>
|
||
<td id="76E37845FF9C5698613EFE25FB5DFE2C" box="[1097,1231,414,429]" gridcol="4" gridrow="7" pageId="5" pageNumber="16">238</td>
|
||
<td id="76E37845FF9C5698602EFE25FA39FE2C" box="[1369,1451,414,429]" gridcol="5" gridrow="7" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE0FFA39FE45" box="[110,1451,436,452]" gridrow="8" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE0FFF08FE45" box="[110,154,436,452]" gridcol="0" gridrow="8" pageId="5" pageNumber="16">8</th>
|
||
<td id="76E37845FF9C56986453FE0FFD8CFE45" box="[292,542,436,452]" gridcol="1" gridrow="8" pageId="5" pageNumber="16">
|
||
(
|
||
<emphasis id="B976CF69FF9CA962645CFE0EFEA7FE45" box="[299,309,437,452]" italics="true" pageId="5" pageNumber="16">R</emphasis>
|
||
/
|
||
<emphasis id="B976CF69FF9CA962644CFE0FFED1FE45" box="[315,323,436,452]" italics="true" pageId="5" pageNumber="16">S</emphasis>
|
||
) 1-butane oxide
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFE0FFD7FFE45" box="[680,749,436,452]" gridcol="2" gridrow="8" pageId="5" pageNumber="16">22,200</td>
|
||
<td id="76E37845FF9C5698660FFE0FFC2CFE45" box="[888,958,436,452]" gridcol="3" gridrow="8" pageId="5" pageNumber="16">5.36</td>
|
||
<td id="76E37845FF9C5698613EFE0FFB5DFE45" box="[1097,1231,436,452]" gridcol="4" gridrow="8" pageId="5" pageNumber="16">241</td>
|
||
<td id="76E37845FF9C5698602EFE0FFA39FE45" box="[1369,1451,436,452]" gridcol="5" gridrow="8" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE77FA39FE5A" box="[110,1451,460,475]" gridrow="9" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE77FF08FE5A" box="[110,154,460,475]" gridcol="0" gridrow="9" pageId="5" pageNumber="16">9</th>
|
||
<td id="76E37845FF9C56986453FE77FD8CFE5A" box="[292,542,460,475]" gridcol="1" gridrow="9" pageId="5" pageNumber="16">1,2,7,8-Diepoxyoctane</td>
|
||
<td id="76E37845FF9C569867DFFE77FD7FFE5A" box="[680,749,460,475]" gridcol="2" gridrow="9" pageId="5" pageNumber="16">4,800</td>
|
||
<td id="76E37845FF9C5698660FFE77FC2CFE5A" box="[888,958,460,475]" gridcol="3" gridrow="9" pageId="5" pageNumber="16">7.12</td>
|
||
<td id="76E37845FF9C5698613EFE77FB5DFE5A" box="[1097,1231,460,475]" gridcol="4" gridrow="9" pageId="5" pageNumber="16">1483</td>
|
||
<td id="76E37845FF9C5698602EFE77FA39FE5A" box="[1369,1451,460,475]" gridcol="5" gridrow="9" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE59FA39FE73" box="[110,1451,482,498]" gridrow="10" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE59FF08FE73" box="[110,154,482,498]" gridcol="0" gridrow="10" pageId="5" pageNumber="16">10</th>
|
||
<td id="76E37845FF9C56986453FE59FD8CFE73" box="[292,542,482,498]" gridcol="1" gridrow="10" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA9626453FE59FEAAFE70" box="[292,312,482,497]" italics="true" pageId="5" pageNumber="16">cis</emphasis>
|
||
-b- Methylstyrene oxide
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFE59FD7FFE73" box="[680,749,482,498]" gridcol="2" gridrow="10" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698660FFE59FC2CFE73" box="[888,958,482,498]" gridcol="3" gridrow="10" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698613EFE59FB5DFE73" box="[1097,1231,482,498]" gridcol="4" gridrow="10" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698602EFE59FA39FE73" box="[1369,1451,482,498]" gridcol="5" gridrow="10" pageId="5" pageNumber="16">3.05</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FE42FA39FD88" box="[110,1451,505,521]" gridrow="11" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FE42FF08FD88" box="[110,154,505,521]" gridcol="0" gridrow="11" pageId="5" pageNumber="16">11</th>
|
||
<td id="76E37845FF9C56986453FE42FD8CFD88" box="[292,542,505,521]" gridcol="1" gridrow="11" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA9626453FE42FED9FD89" box="[292,331,505,520]" italics="true" pageId="5" pageNumber="16">trans</emphasis>
|
||
-b- Methylstyrene oxide-
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFE42FD7FFD88" box="[680,749,505,521]" gridcol="2" gridrow="11" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698660FFE42FC2CFD88" box="[888,958,505,521]" gridcol="3" gridrow="11" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698613EFE42FB5DFD88" box="[1097,1231,505,521]" gridcol="4" gridrow="11" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698602EFE42FA39FD88" box="[1369,1451,505,521]" gridcol="5" gridrow="11" pageId="5" pageNumber="16">14.28</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FDABFA39FDA1" box="[110,1451,528,544]" gridrow="12" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FDABFF08FDA1" box="[110,154,528,544]" gridcol="0" gridrow="12" pageId="5" pageNumber="16">12</th>
|
||
<td id="76E37845FF9C56986453FDABFD8CFDA1" box="[292,542,528,544]" gridcol="1" gridrow="12" pageId="5" pageNumber="16">b- Dimethylstyrene oxide</td>
|
||
<td id="76E37845FF9C569867DFFDABFD7FFDA1" box="[680,749,528,544]" gridcol="2" gridrow="12" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698660FFDABFC2CFDA1" box="[888,958,528,544]" gridcol="3" gridrow="12" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698613EFDABFB5DFDA1" box="[1097,1231,528,544]" gridcol="4" gridrow="12" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698602EFDABFA39FDA1" box="[1369,1451,528,544]" gridcol="5" gridrow="12" pageId="5" pageNumber="16">6.99</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FD9CFA39FDB7" box="[110,1451,551,566]" gridrow="13" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FD9CFF08FDB7" box="[110,154,551,566]" gridcol="0" gridrow="13" pageId="5" pageNumber="16">13</th>
|
||
<td id="76E37845FF9C56986453FD9CFD8CFDB7" box="[292,542,551,566]" gridcol="1" gridrow="13" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA9626453FD9CFEAAFDB7" box="[292,312,551,566]" italics="true" pageId="5" pageNumber="16">cis</emphasis>
|
||
-2,3-Epoxybutane
|
||
</td>
|
||
<td id="76E37845FF9C569867DFFD9CFD7FFDB7" box="[680,749,551,566]" gridcol="2" gridrow="13" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698660FFD9CFC2CFDB7" box="[888,958,551,566]" gridcol="3" gridrow="13" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698613EFD9CFB5DFDB7" box="[1097,1231,551,566]" gridcol="4" gridrow="13" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698602EFD9CFA39FDB7" box="[1369,1451,551,566]" gridcol="5" gridrow="13" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
<tr id="35321139FF9C56986519FD85FA39FDCC" box="[110,1451,574,589]" gridrow="14" pageId="5" pageNumber="16">
|
||
<th id="76E37845FF9C56986519FD85FF08FDCC" box="[110,154,574,589]" gridcol="0" gridrow="14" pageId="5" pageNumber="16">14</th>
|
||
<td id="76E37845FF9C56986453FD85FD8CFDCC" box="[292,542,574,589]" gridcol="1" gridrow="14" pageId="5" pageNumber="16">2,3-Dimethyl-2,3-epoxybutane</td>
|
||
<td id="76E37845FF9C569867DFFD85FD7FFDCC" box="[680,749,574,589]" gridcol="2" gridrow="14" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698660FFD85FC2CFDCC" box="[888,958,574,589]" gridcol="3" gridrow="14" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698613EFD85FB5DFDCC" box="[1097,1231,574,589]" gridcol="4" gridrow="14" pageId="5" pageNumber="16">–</td>
|
||
<td id="76E37845FF9C5698602EFD85FA39FDCC" box="[1369,1451,574,589]" gridcol="5" gridrow="14" pageId="5" pageNumber="16">–</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<caption id="DF7D43F3FF9CA96265F1FC95FD55FCBC" ID-DOI="http://doi.org/10.5281/zenodo.10514931" ID-Zenodo-Dep="10514931" box="[134,711,814,829]" httpUri="https://zenodo.org/record/10514931/files/figure.png" pageId="5" pageNumber="16" startId="5.[134,199,814,828]" targetBox="[122,725,656,782]" targetPageId="5">
|
||
<paragraph id="8BBD137BFF9CA96265F1FC95FD55FCBC" blockId="5.[134,711,814,829]" box="[134,711,814,829]" pageId="5" pageNumber="16">
|
||
<emphasis id="B976CF69FF9CA96265F1FC95FF4EFCBD" bold="true" box="[134,220,814,828]" pageId="5" pageNumber="16">Scheme 4.</emphasis>
|
||
Regioisomeric cyclizations of
|
||
<emphasis id="B976CF69FF9CA96264A2FC95FE6EFCBC" box="[469,508,814,829]" italics="true" pageId="5" pageNumber="16">trans</emphasis>
|
||
-4,5-epoxy-hexanol (
|
||
<emphasis id="B976CF69FF9CA96267D0FC95FD29FCBD" bold="true" box="[679,699,814,828]" pageId="5" pageNumber="16">10</emphasis>
|
||
).
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8BBD137BFF9CA9626501FBA7FED8FAAB" blockId="5.[87,757,857,1322]" pageId="5" pageNumber="16">
|
||
The ability of the
|
||
<taxonomicName id="4C0268F8FF9CA9626447FBA0FE16FBAE" authority="EH" authorityName="EH" box="[304,388,1051,1071]" class="Insecta" family="Cicadidae" genus="Karenia" kingdom="Animalia" order="Hemiptera" pageId="5" pageNumber="16" phylum="Arthropoda" rank="species" species="brevis">
|
||
<emphasis id="B976CF69FF9CA9626447FBA0FE16FBAE" box="[304,388,1051,1071]" italics="true" pageId="5" pageNumber="16">K. brevis</emphasis>
|
||
</taxonomicName>
|
||
EH to perform cyclization was also evaluated. The substrate
|
||
<emphasis id="B976CF69FF9CA962642FFB8CFE1BFBCA" box="[344,393,1079,1099]" italics="true" pageId="5" pageNumber="16">trans</emphasis>
|
||
-4,5-epoxy-hexanol
|
||
<emphasis id="B976CF69FF9CA9626721FB83FDF1FBCA" bold="true" box="[598,611,1080,1099]" pageId="5" pageNumber="16">9</emphasis>
|
||
was prepared as previously described (
|
||
<bibRefCitation id="EF936E8AFF9CA9626428FBEFFDB2FBE6" author="Coxon, J. M. & Hartshorn, M. P. & Swallow, W." box="[351,544,1108,1127]" pageId="5" pageNumber="16" pagination="2521 - 2526" refId="ref10467" refString="Coxon, J. M., Hartshorn, M. P., Swallow, W., 1973. Study of hydroxyl participation in acyclic epoxide systems-acid-catalyzed rearrangements of trans- 3,4 - epoxypentan- 1 ols, and cis- 3,4 - epoxypentan- 1 - ols, 4,5 - epoxyhexan- 1 - ols, and 5,6 - epoxyheptan- 1 - ols. Aust. J. Chem. 26, 2521 - 2526." type="journal article" year="1973">Coxon et al., 1973</bibRefCitation>
|
||
).This substrate may undergo
|
||
<emphasis id="B976CF69FF9CA96265CEFBD4FE98FB02" box="[185,266,1135,1155]" italics="true" pageId="5" pageNumber="16">endo-tet</emphasis>
|
||
cyclization to produce pyran
|
||
<emphasis id="B976CF69FF9CA9626716FBCBFDE8FB02" bold="true" box="[609,634,1136,1155]" pageId="5" pageNumber="16">10</emphasis>
|
||
, or
|
||
<emphasis id="B976CF69FF9CA96267C6FBD4FD66FB02" box="[689,756,1135,1155]" italics="true" pageId="5" pageNumber="16">exo-tet</emphasis>
|
||
cyclization to produce furan
|
||
<emphasis id="B976CF69FF9CA9626403FB30FE1FFB1F" bold="true" box="[372,397,1163,1182]" pageId="5" pageNumber="16">11</emphasis>
|
||
(
|
||
<figureCitation id="13390FFEFF9CA96264ECFB37FE69FB1E" box="[411,507,1164,1183]" captionStart="Scheme 4" captionStartId="5.[134,199,814,828]" captionTargetBox="[122,725,656,782]" captionTargetId="figure-763@5.[119,725,656,785]" captionTargetPageId="5" captionText="Scheme 4. Regioisomeric cyclizations of trans-4,5-epoxy-hexanol (10)." figureDoi="http://doi.org/10.5281/zenodo.10514931" httpUri="https://zenodo.org/record/10514931/files/figure.png" pageId="5" pageNumber="16">Scheme 4</figureCitation>
|
||
).The substrate was incubated with the expressed EH in reaction buffer and the reaction was monitored by GC–MS. Both possible products were identified by GC–MS, by comparison with authentic samples however, neither the percent conversion nor the product ratio differed from that of the buffer alone.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |