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132 lines
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<document id="A99BF2F3240BA3C8849BD8921D45CB33" ID-DOI="10.1016/j.phytochem.2020.112626" ID-ISSN="1873-3700" ID-Zenodo-Dep="8291734" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="valdenar" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="valdenar" IM.taxonomicNames_approvedBy="valdenar" IM.treatments_approvedBy="valdenar" checkinTime="1693246558342" checkinUser="felipe" docAuthor="Miller, Justin C., Hollatz, Allison J. & Schuler, Mary A." docDate="2021" docId="8D608791DF6D136FFFCD2D0BFD77B080" docLanguage="en" docName="Phytochemistry.183.112626.pdf" docOrigin="Phytochemistry (112626) 183" docSource="http://dx.doi.org/10.1016/j.phytochem.2020.112626" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.5:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="5" docTitle="Camptotheca" docType="treatment" docVersion="3" lastPageNumber="10" masterDocId="7159FFE9DF641366FFA92F64FFB3B679" masterDocTitle="P 450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata" masterLastPageNumber="13" masterPageNumber="1" pageNumber="10" updateTime="1693411865241" updateUser="valdenar">
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<mods:title id="69FE18A03C0D82775D8DB3230246DDF5">P 450 variations bifurcate the early terpene indole alkaloid pathway in Catharanthus roseus and Camptotheca acuminata</mods:title>
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<mods:name id="B2FECCE6119FD83940A4F06954B18EE7" type="personal">
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<mods:namePart id="97856620DC36B4C3215AC962942D2B9B">Miller, Justin C.</mods:namePart>
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<mods:affiliation id="BB2C81936F898C231AF4CAC1BFE1F2F6">Department of Chemistry, University of Illinois at Urbana-Champaign, 1201 W. Gregory Dr., 162 Edward R. Madigan Laboratory (ERML), Urbana, IL, 61801, USA</mods:affiliation>
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<mods:namePart id="2A5A2D9D44746B1DE92A240393D24780">Hollatz, Allison J.</mods:namePart>
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<mods:namePart id="F1DB60B0969F180CB961843FA13B7A96">Schuler, Mary A.</mods:namePart>
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<mods:typeOfResource id="8E415612756AD72E36DCDDC7F0BC564E">text</mods:typeOfResource>
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<mods:title id="F305F7B87293F2E585354309D467309C">Phytochemistry</mods:title>
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<mods:part id="ACE9BF3E39E8DA2BFD5DB0D9C3EA6C56">
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<mods:date id="C3EA43BF055AA21CE6BD99E6C0B20BD9">2021</mods:date>
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<mods:title id="7F139C1D32D48B7B8DC48050060459B9">112626</mods:title>
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<mods:number id="5FD60E04368CD6CCE30D0AB98F90AE3A">2021-03-31</mods:number>
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<mods:number id="700467FC88934149E0B1923B9CF4C43D">183</mods:number>
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<mods:url id="47661FAB5E51117C04BB3DD7F8B935B3">http://dx.doi.org/10.1016/j.phytochem.2020.112626</mods:url>
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<mods:identifier id="CEC4051220C3093E9B4BEEF64C536660" type="DOI">10.1016/j.phytochem.2020.112626</mods:identifier>
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<mods:identifier id="58C0EE82E5D88A7DD7D361C4DF4D4712" type="ISSN">1873-3700</mods:identifier>
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<treatment id="8D608791DF6D136FFFCD2D0BFD77B080" LSID="urn:lsid:plazi:treatment:8D608791DF6D136FFFCD2D0BFD77B080" httpUri="http://treatment.plazi.org/id/8D608791DF6D136FFFCD2D0BFD77B080" lastPageNumber="10" pageId="9" pageNumber="10">
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<subSubSection id="4DD3650CDF6D136FFFCD2D0BFD9AB4FB" box="[100,553,622,642]" pageId="9" pageNumber="10" type="nomenclature">
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<paragraph id="05763687DF6D136FFFCD2D0BFD9AB4FB" blockId="9.[100,553,622,642]" box="[100,553,622,642]" pageId="9" pageNumber="10">
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<heading id="5E3E81EBDF6D136FFFCD2D0BFD9AB4FB" bold="true" box="[100,553,622,642]" fontSize="36" level="1" pageId="9" pageNumber="10" reason="1">
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<emphasis id="37BDEA95DF6D136FFFCD2D0BFD9AB4FB" bold="true" box="[100,553,622,642]" italics="true" pageId="9" pageNumber="10">
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3.5. Broad substrate scope of
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<taxonomicName id="C2C94D04DF6D136FFEDE2D0AFE58B4F8" ID-CoL="8VVXT" ID-ENA="16921" box="[375,491,622,641]" class="Magnoliopsida" family="Nyssaceae" genus="Camptotheca" kingdom="Plantae" order="Cornales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">Camptotheca</taxonomicName>
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SLASs
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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="4DD3650CDF6D136FFF2D2DC3FD77B080" pageId="9" pageNumber="10" type="description">
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<paragraph id="05763687DF6D136FFF2D2DC3FE4AB238" blockId="9.[100,770,679,1786]" pageId="9" pageNumber="10">
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Despite their ability to modify both unmethylated and methylated derivatives of loganic acid, metabolomic data have indicated that multiple
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<taxonomicName id="C2C94D04DF6D136FFF302DBAFEBEB488" box="[153,269,734,753]" class="Magnoliopsida" family="Nyssaceae" genus="Camptotheca" kingdom="Plantae" order="Cornales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFF302DBAFEBEB488" bold="true" box="[153,269,734,753]" italics="true" pageId="9" pageNumber="10">Camptotheca</emphasis>
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</taxonomicName>
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tissues contain loganic acid, secologanic acid and strictosidinic acid but not loganin, secologanin or strictosidine (
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<bibRefCitation id="61584B76DF6D136FFD642D9EFF62B550" author="Sadre, R. & Magallanes-Lundback, M. & Pradhan, S. & Salim, V. & Mesberg, A. & Jones, A. D. & DellaPenna, D." pageId="9" pageNumber="10" pagination="1926 - 1944" refId="ref15314" refString="Sadre, R., Magallanes-Lundback, M., Pradhan, S., Salim, V., Mesberg, A., Jones, A. D., DellaPenna, D., 2016. Metabolite diversity in alkaloid biosynthesis: a multilane (diastereomer) highway for camptothecin synthesis in Camptotheca acuminata. Plant Cell 28, 1926 - 1944. https: // doi. org / 10.1105 / tpc. 16.00193." type="journal article" year="2016">Sadre et al., 2016</bibRefCitation>
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). Additional metabolomic data from
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<bibRefCitation id="61584B76DF6D136FFD9D2C72FD7DB550" author="Jin, Z. & Cong, Y. & Zhu, S. & Xing, R. & Zhang, D. & Yao, X. & Wan, R. & Wang, Y. & Yu, F." box="[564,718,790,810]" pageId="9" pageNumber="10" pagination="1098 - 1108" refId="ref14282" refString="Jin, Z., Cong, Y., Zhu, S., Xing, R., Zhang, D., Yao, X., Wan, R., Wang, Y., Yu, F., 2019. Two classes of cytochrome P 450 reductase genes and their divergent functions in Camptotheca acuminata Decne. Int. J. Biol. Macromol. 138, 1098 - 1108. https: // doi. org / 10.1016 / j. ijbiomac. 2019.07.141." type="journal article" year="2019">Jin et al. (2019)</bibRefCitation>
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have verified the presence of loganic acid, secologanic acid and strictosidinic acid in shoot apices and leaves but not in roots. The use of these unmethylated precursors for the formation of subsequent products represents an important bifurcation in the
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<taxonomicName id="C2C94D04DF6D136FFDA92CE1FDC7B5E1" box="[512,628,901,920]" class="Magnoliopsida" family="Nyssaceae" genus="Camptotheca" kingdom="Plantae" order="Cornales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFDA92CE1FDC7B5E1" bold="true" box="[512,628,901,920]" italics="true" pageId="9" pageNumber="10">Camptotheca</emphasis>
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</taxonomicName>
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pathway from the use of methylated precursors in
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<taxonomicName id="C2C94D04DF6D136FFE6F2CC5FD8DB5CD" box="[454,574,929,948]" class="Magnoliopsida" family="Apocynaceae" genus="Catharanthus" kingdom="Plantae" order="Gentianales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFE6F2CC5FD8DB5CD" bold="true" box="[454,574,929,948]" italics="true" pageId="9" pageNumber="10">Catharanthus</emphasis>
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</taxonomicName>
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,
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<taxonomicName id="C2C94D04DF6D136FFDE42CC5FD2AB5CD" box="[589,665,929,948]" class="Magnoliopsida" family="Caprifoliaceae" genus="Lonicera" kingdom="Plantae" order="Dipsacales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFDE42CC5FD2AB5CD" bold="true" box="[589,665,929,948]" italics="true" pageId="9" pageNumber="10">Lonicera</emphasis>
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</taxonomicName>
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and many other medicinal plant species. Presuming that loganin does not exist in
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<taxonomicName id="C2C94D04DF6D136FFFCD2CBDFF6BB595" box="[100,216,985,1004]" class="Magnoliopsida" family="Nyssaceae" genus="Camptotheca" kingdom="Plantae" order="Cornales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFFCD2CBDFF6BB595" bold="true" box="[100,216,985,1004]" italics="true" pageId="9" pageNumber="10">Camptotheca</emphasis>
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</taxonomicName>
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even at low levels, the ability of CYP72A564 and CYP72A565 to metabolize loganin is surprising and indicates that it has retained an ancestral activity (toward loganin) while obtaining another activity (toward loganic acid) or
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<emphasis id="37BDEA95DF6D136FFE342B49FE40B239" bold="true" box="[413,499,1069,1088]" italics="true" pageId="9" pageNumber="10">vice versa</emphasis>
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.
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</paragraph>
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<paragraph id="05763687DF6D136FFF2D2B2DFD93B3F6" blockId="9.[100,770,679,1786]" pageId="9" pageNumber="10">
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<taxonomicName id="C2C94D04DF6D136FFF2D2B2DFF4BB225" box="[132,248,1097,1116]" class="Magnoliopsida" family="Nyssaceae" genus="Camptotheca" kingdom="Plantae" order="Cornales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFF2D2B2DFF4BB225" bold="true" box="[132,248,1097,1116]" italics="true" pageId="9" pageNumber="10">Camptotheca</emphasis>
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</taxonomicName>
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SLASs have also been reported to hydroxylate 7-deoxyloganic acid to form loganic acid (
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<bibRefCitation id="61584B76DF6D136FFE0D2B01FDF0B201" author="Yang, Y. & Li, W. & Pang, J. & Jiang, L. & Qu, X. & Pu, X. & Zhang, G. & Luo, Y." box="[420,579,1125,1144]" pageId="9" pageNumber="10" pagination="1091 - 1096" refId="ref15782" refString="Yang, Y., Li, W., Pang, J., Jiang, L., Qu, X., Pu, X., Zhang, G., Luo, Y., 2019. Bifunctional cytochrome P 450 enzymes involved in camptothecin biosynthesis. ACS Chem. Biol. 14, 1091 - 1096. https: // doi. org / 10.1021 / acschembio. 8 b 01124." type="journal article" year="2019">Yang et al., 2019</bibRefCitation>
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), the preceding step in their TIA pathway. Lacking access to 7-deoxyloganic acid to assess 7-hydroxylation activities of these CYPs, we used the structurally-related geniposide documented as an alternate substrate by Yang and colleagues. Not only did CYP72A564 and CYP72A565 hydroxylate geniposide,
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<taxonomicName id="C2C94D04DF6D136FFE9F2B94FE52B37A" authority="CYP" authorityName="CYP" box="[310,481,1264,1283]" class="Magnoliopsida" family="Apocynaceae" genus="Catharanthus" kingdom="Plantae" order="Gentianales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFE9F2B94FE1DB37A" bold="true" box="[310,430,1264,1283]" italics="true" pageId="9" pageNumber="10">Catharanthus</emphasis>
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CYP
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</taxonomicName>
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72A1 produced the same product (Supplemental Fig. S13). Assuming geniposide turnover is a quality surrogate for 7-deoxyloganin hydroxylation, this last result is in direct contrast to that of
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<bibRefCitation id="61584B76DF6D136FFEBB2A20FE74B32E" author="Irmler, S. & St-Pierre, B. & Crouch, N. P. & Hotze, M. & Schmidt, J. & Strack, D. & Matern, U." box="[274,455,1348,1367]" pageId="9" pageNumber="10" pagination="797 - 804" refId="ref14096" refString="Irmler, S., Schr ¨ oder, G., St-Pierre, B., Crouch, N. P., Hotze, M., Schmidt, J., Strack, D., Matern, U., Schroder ¨, J., 2000. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P 450 CYP 72 A 1 as secologanin synthase. Plant J. 24, 797 - 804. https: // doi. org / 10.1111 / j. 1365 - 313 X. 2000.00922. x." type="journal article" year="2000">Irmler et al. (2000)</bibRefCitation>
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who recorded no 7-deoxyloganin hydroxylation by an
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<emphasis id="37BDEA95DF6D136FFE862A04FEDBB30B" bold="true" box="[303,360,1375,1395]" italics="true" pageId="9" pageNumber="10">E. coli</emphasis>
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membrane fraction containing a fusion of
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<taxonomicName id="C2C94D04DF6D136FFFCD2A1FFEBCB3F6" authority="CYP" authorityName="CYP" box="[100,271,1403,1423]" class="Magnoliopsida" family="Apocynaceae" genus="Catharanthus" kingdom="Plantae" order="Gentianales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFFCD2A1FFF6FB3F7" bold="true" box="[100,220,1403,1422]" italics="true" pageId="9" pageNumber="10">Catharanthus</emphasis>
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CYP
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</taxonomicName>
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72A1 with
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<taxonomicName id="C2C94D04DF6D136FFEDA2A1FFD93B3F6" authority="CPR." box="[371,544,1403,1423]" class="Magnoliopsida" family="Apocynaceae" genus="Catharanthus" kingdom="Plantae" order="Gentianales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFEDA2A1FFE58B3F7" bold="true" box="[371,491,1403,1422]" italics="true" pageId="9" pageNumber="10">Catharanthus</emphasis>
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CPR.
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</taxonomicName>
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</paragraph>
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<paragraph id="05763687DF6D136FFF2D2AFCFD77B080" blockId="9.[100,770,679,1786]" pageId="9" pageNumber="10">
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With this additional 7DLH activity confirmed for the
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<taxonomicName id="C2C94D04DF6D136FFD272AF3FCB1B3D3" box="[654,770,1431,1450]" class="Magnoliopsida" family="Nyssaceae" genus="Camptotheca" kingdom="Plantae" order="Cornales" pageId="9" pageNumber="10" phylum="Tracheophyta" rank="genus">
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<emphasis id="37BDEA95DF6D136FFD272AF3FCB1B3D3" bold="true" box="[654,770,1431,1450]" italics="true" pageId="9" pageNumber="10">Camptotheca</emphasis>
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</taxonomicName>
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SLASs, we have docked 7-deoxyloganin in CYP72A564 and CYP72A565 to determine whether predicted substrate contacts for their hydroxylation activities differ from those for carbon-carbon bond scission activities on loganic acid and loganin. These dockings (Supplemental Fig. S12) show little variation in the binding poses for these various molecules near the heme. Though there are differences in contacts when comparing 7-deoxyloganic acid and loganic acid, contacts with the strongest interactions such as His132 H-bonding to the carboxylic acid moiety of both compounds remain. These similiarities in binding position and interaction are unsurprising given the close proximity of C7 and C10 on the iridoid scaffold, either of which are required to be in close proximity to the iron(IV)-oxo complex for hydrogen abstraction.
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</paragraph>
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</subSubSection>
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</treatment>
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</document> |