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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Substrate analog studies of the ω-regiospecificity of <italic>Mycobacterium tuberculosis</italic> cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1</title><author><name sortKey="Johnston, Jonathan B" sort="Johnston, Jonathan B" uniqKey="Johnston J" first="Jonathan B." last="Johnston">Jonathan B. Johnston</name><affiliation><nlm:aff id="A1">Department of Pharmaceutical Chemistry, University of California San Francisco, San Francisco 94158-2517 U.S.A</nlm:aff></affiliation></author><author><name sortKey="Singh, Arti A" sort="Singh, Arti A" uniqKey="Singh A" first="Arti A." last="Singh">Arti A. Singh</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="Clary, Anaelle A" sort="Clary, Anaelle A" uniqKey="Clary A" first="Anaelle A." last="Clary">Anaelle A. Clary</name><affiliation><nlm:aff id="A3">Bioengineering Department, Polytech Nice-Sophia, Antipolis Cedex 06903, France</nlm:aff></affiliation></author><author><name sortKey="Chen, Chiung Kuan" sort="Chen, Chiung Kuan" uniqKey="Chen C" first="Chiung-Kuan" last="Chen">Chiung-Kuan Chen</name><affiliation><nlm:aff id="A4">Department of Molecular Biology & Biochemistry, University of California Irvine, Irvine 92697, U.S.A</nlm:aff></affiliation></author><author><name sortKey="Hayes, Patricia Y" sort="Hayes, Patricia Y" uniqKey="Hayes P" first="Patricia Y." last="Hayes">Patricia Y. Hayes</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="Chow, Sharon" sort="Chow, Sharon" uniqKey="Chow S" first="Sharon" last="Chow">Sharon Chow</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="De Voss, James J" sort="De Voss, James J" uniqKey="De Voss J" first="James J." last="De Voss">James J. De Voss</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="Ortiz De Montellano, Paul R" sort="Ortiz De Montellano, Paul R" uniqKey="Ortiz De Montellano P" first="Paul R." last="Ortiz De Montellano">Paul R. Ortiz De Montellano</name><affiliation><nlm:aff id="A1">Department of Pharmaceutical Chemistry, University of California San Francisco, San Francisco 94158-2517 U.S.A</nlm:aff></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">22647881</idno><idno type="pmc">3376231</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3376231</idno><idno type="RBID">PMC:3376231</idno><idno type="doi">10.1016/j.bmc.2012.05.003</idno><date when="2012">2012</date><idno type="wicri:Area/Pmc/Corpus">002163</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">002163</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Substrate analog studies of the ω-regiospecificity of <italic>Mycobacterium tuberculosis</italic> cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1</title><author><name sortKey="Johnston, Jonathan B" sort="Johnston, Jonathan B" uniqKey="Johnston J" first="Jonathan B." last="Johnston">Jonathan B. Johnston</name><affiliation><nlm:aff id="A1">Department of Pharmaceutical Chemistry, University of California San Francisco, San Francisco 94158-2517 U.S.A</nlm:aff></affiliation></author><author><name sortKey="Singh, Arti A" sort="Singh, Arti A" uniqKey="Singh A" first="Arti A." last="Singh">Arti A. Singh</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="Clary, Anaelle A" sort="Clary, Anaelle A" uniqKey="Clary A" first="Anaelle A." last="Clary">Anaelle A. Clary</name><affiliation><nlm:aff id="A3">Bioengineering Department, Polytech Nice-Sophia, Antipolis Cedex 06903, France</nlm:aff></affiliation></author><author><name sortKey="Chen, Chiung Kuan" sort="Chen, Chiung Kuan" uniqKey="Chen C" first="Chiung-Kuan" last="Chen">Chiung-Kuan Chen</name><affiliation><nlm:aff id="A4">Department of Molecular Biology & Biochemistry, University of California Irvine, Irvine 92697, U.S.A</nlm:aff></affiliation></author><author><name sortKey="Hayes, Patricia Y" sort="Hayes, Patricia Y" uniqKey="Hayes P" first="Patricia Y." last="Hayes">Patricia Y. Hayes</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="Chow, Sharon" sort="Chow, Sharon" uniqKey="Chow S" first="Sharon" last="Chow">Sharon Chow</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="De Voss, James J" sort="De Voss, James J" uniqKey="De Voss J" first="James J." last="De Voss">James J. De Voss</name><affiliation><nlm:aff id="A2">School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</nlm:aff></affiliation></author><author><name sortKey="Ortiz De Montellano, Paul R" sort="Ortiz De Montellano, Paul R" uniqKey="Ortiz De Montellano P" first="Paul R." last="Ortiz De Montellano">Paul R. Ortiz De Montellano</name><affiliation><nlm:aff id="A1">Department of Pharmaceutical Chemistry, University of California San Francisco, San Francisco 94158-2517 U.S.A</nlm:aff></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="ISSN">0968-0896</idno><idno type="eISSN">1464-3391</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p id="P2">We report the synthesis and evaluation of a series of cholesterol side-chain analogs as mechanistic probes of three important <italic>Mycobacterium tuberculosis</italic> cytochrome P450 enzymes that selectively oxidize the ω-position of the methyl-branched cholesterol side-chain. To probe the structural requirements for the thermodynamically disfavored ω-regiospecificity we compared the binding of these substrate analogs to each P450, determined the turnover rates, and characterized the enzymatic products. The results are discussed in the context of the structure-activity relationships of the enzymes and how their active sites enforce ω-oxidation.</p></div></front></TEI><pmc article-type="research-article"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
<pmc-dir>properties manuscript</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-journal-id">9413298</journal-id><journal-id journal-id-type="pubmed-jr-id">8539</journal-id><journal-id journal-id-type="nlm-ta">Bioorg Med Chem</journal-id><journal-id journal-id-type="iso-abbrev">Bioorg. Med. Chem.</journal-id><journal-title-group><journal-title>Bioorganic & medicinal chemistry</journal-title></journal-title-group><issn pub-type="ppub">0968-0896</issn><issn pub-type="epub">1464-3391</issn></journal-meta><article-meta><article-id pub-id-type="pmid">22647881</article-id><article-id pub-id-type="pmc">3376231</article-id><article-id pub-id-type="doi">10.1016/j.bmc.2012.05.003</article-id><article-id pub-id-type="manuscript">NIHMS376911</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Substrate analog studies of the ω-regiospecificity of <italic>Mycobacterium tuberculosis</italic> cholesterol metabolizing cytochrome P450 enzymes CYP124A1, CYP125A1 and CYP142A1</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Johnston</surname><given-names>Jonathan B.</given-names></name><xref ref-type="aff" rid="A1">a</xref></contrib><contrib contrib-type="author"><name><surname>Singh</surname><given-names>Arti A.</given-names></name><xref ref-type="aff" rid="A2">b</xref></contrib><contrib contrib-type="author"><name><surname>Clary</surname><given-names>Anaelle A.</given-names></name><xref ref-type="aff" rid="A3">c</xref></contrib><contrib contrib-type="author"><name><surname>Chen</surname><given-names>Chiung-Kuan</given-names></name><xref ref-type="aff" rid="A4">d</xref></contrib><contrib contrib-type="author"><name><surname>Hayes</surname><given-names>Patricia Y.</given-names></name><xref ref-type="aff" rid="A2">b</xref></contrib><contrib contrib-type="author"><name><surname>Chow</surname><given-names>Sharon</given-names></name><xref ref-type="aff" rid="A2">b</xref></contrib><contrib contrib-type="author"><name><surname>De Voss</surname><given-names>James J.</given-names></name><xref ref-type="aff" rid="A2">b</xref></contrib><contrib contrib-type="author"><name><surname>Ortiz de Montellano</surname><given-names>Paul R.</given-names></name><xref ref-type="aff" rid="A1">a</xref><xref rid="FN1" ref-type="author-notes">*</xref></contrib></contrib-group><aff id="A1"><label>a</label>Department of Pharmaceutical Chemistry, University of California San Francisco, San Francisco 94158-2517 U.S.A</aff><aff id="A2"><label>b</label>School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, 4072, Australia</aff><aff id="A3"><label>c</label>Bioengineering Department, Polytech Nice-Sophia, Antipolis Cedex 06903, France</aff><aff id="A4"><label>d</label>Department of Molecular Biology & Biochemistry, University of California Irvine, Irvine 92697, U.S.A</aff><author-notes><corresp id="FN1"><label>*</label>Corresponding author. Tel.: 415-476-2903; fax: 415-502-4728; <email>ortiz@cgl.ucsf.edu</email></corresp></author-notes><pub-date pub-type="nihms-submitted"><day>14</day><month>5</month><year>2012</year></pub-date><pub-date pub-type="epub"><day>11</day><month>5</month><year>2012</year></pub-date><pub-date pub-type="ppub"><day>1</day><month>7</month><year>2012</year></pub-date><pub-date pub-type="pmc-release"><day>01</day><month>7</month><year>2013</year></pub-date><volume>20</volume><issue>13</issue><fpage>4064</fpage><lpage>4081</lpage><permissions><copyright-statement>© 2012 Elsevier Ltd. All rights reserved.</copyright-statement><copyright-year>2012</copyright-year></permissions><abstract><p id="P2">We report the synthesis and evaluation of a series of cholesterol side-chain analogs as mechanistic probes of three important <italic>Mycobacterium tuberculosis</italic> cytochrome P450 enzymes that selectively oxidize the ω-position of the methyl-branched cholesterol side-chain. To probe the structural requirements for the thermodynamically disfavored ω-regiospecificity we compared the binding of these substrate analogs to each P450, determined the turnover rates, and characterized the enzymatic products. The results are discussed in the context of the structure-activity relationships of the enzymes and how their active sites enforce ω-oxidation.</p></abstract><kwd-group><kwd><italic>Mycobacterium tuberculosis</italic></kwd><kwd>cytochrome P450</kwd><kwd>substrate analog</kwd><kwd>steroid</kwd><kwd>ω-oxidation</kwd></kwd-group><funding-group><award-group><funding-source country="United States">National Institute of Allergy and Infectious Diseases Extramural Activities : NIAID</funding-source><award-id>R01 AI074824 || AI</award-id></award-group></funding-group></article-meta></front></pmc></record>Pour manipuler ce document sous Unix (Dilib)
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