Systematic Comparison of Sets of 13C NMR Spectra That Are Potentially Identical. Confirmation of the Configuration of a Cuticular Hydrocarbon from the Cane Beetle Antitrogus parvulus
Identifieur interne : 001048 ( Main/Exploration ); précédent : 001047; suivant : 001049Systematic Comparison of Sets of 13C NMR Spectra That Are Potentially Identical. Confirmation of the Configuration of a Cuticular Hydrocarbon from the Cane Beetle Antitrogus parvulus
Auteurs : Norazah Basar [Malaisie] ; Krishnan Damodaran [États-Unis] ; Hao Liu [Royaume-Uni] ; Gareth X0a A. Morris [Royaume-Uni] ; Hasnah M. Sirat [Malaisie] ; Eric J. Thomas [Royaume-Uni] ; Dennis P. Curran [États-Unis]Source :
- The Journal of Organic Chemistry [ 0022-3263 ] ; 2014.
Abstract
A systematic process is introduced
to compare 13C NMR
spectra of two (or more) candidate samples of known structure to a
natural product sample of unknown structure. The process is designed
for the case where the spectra involved can reasonably be expected
to be very similar, perhaps even identical. It is first validated
by using published 13C NMR data sets for the natural product
4,6,8,10,16,18-hexamethyldocosane. Then the stereoselective total
syntheses of two candidate isomers of the related 4,6,8,10,16-pentamethyldocosane
natural product are described, and the process is applied to confidently
assign the configuration of the natural product as (4
Url:
DOI: 10.1021/jo5012027
PubMed: 25019530
PubMed Central: 4136713
Affiliations:
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parvulus</italic></title><author><name sortKey="Basar, Norazah" sort="Basar, Norazah" uniqKey="Basar N" first="Norazah" last="Basar">Norazah Basar</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry, Faculty of Science,<institution>Universiti Teknologi Malaysia</institution>, Skudai, 81310 Johor,<country>Malaysia</country></nlm:aff><country xml:lang="fr">Malaisie</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Damodaran, Krishnan" sort="Damodaran, Krishnan" uniqKey="Damodaran K" first="Krishnan" last="Damodaran">Krishnan Damodaran</name><affiliation wicri:level="1"><nlm:aff id="aff2">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Liu, Hao" sort="Liu, Hao" uniqKey="Liu H" first="Hao" last="Liu">Hao Liu</name><affiliation wicri:level="1"><nlm:aff id="aff3">School of Chemistry,<institution>University of Manchester</institution>, Manchester M13 9PL,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Morris, Gareth X0a A" sort="Morris, Gareth X0a A" uniqKey="Morris G" first="Gareth X0a A." last="Morris">Gareth X0a A. Morris</name><affiliation wicri:level="1"><nlm:aff id="aff3">School of Chemistry,<institution>University of Manchester</institution>, Manchester M13 9PL,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Sirat, Hasnah M" sort="Sirat, Hasnah M" uniqKey="Sirat H" first="Hasnah M." last="Sirat">Hasnah M. Sirat</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry, Faculty of Science,<institution>Universiti Teknologi Malaysia</institution>, Skudai, 81310 Johor,<country>Malaysia</country></nlm:aff><country xml:lang="fr">Malaisie</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Thomas, Eric J" sort="Thomas, Eric J" uniqKey="Thomas E" first="Eric J." last="Thomas">Eric J. Thomas</name><affiliation wicri:level="1"><nlm:aff id="aff3">School of Chemistry,<institution>University of Manchester</institution>, Manchester M13 9PL,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Curran, Dennis P" sort="Curran, Dennis P" uniqKey="Curran D" first="Dennis P." last="Curran">Dennis P. Curran</name><affiliation wicri:level="1"><nlm:aff id="aff2">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">25019530</idno><idno type="pmc">4136713</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4136713</idno><idno type="RBID">PMC:4136713</idno><idno type="doi">10.1021/jo5012027</idno><date when="2014">2014</date><idno type="wicri:Area/Pmc/Corpus">000345</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000345</idno><idno type="wicri:Area/Pmc/Curation">000345</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000345</idno><idno type="wicri:Area/Pmc/Checkpoint">000461</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000461</idno><idno type="wicri:Area/Ncbi/Merge">002990</idno><idno type="wicri:Area/Ncbi/Curation">002990</idno><idno type="wicri:Area/Ncbi/Checkpoint">002990</idno><idno type="wicri:doubleKey">0022-3263:2014:Basar N:systematic:comparison:of</idno><idno type="wicri:Area/Main/Merge">001071</idno><idno type="wicri:Area/Main/Curation">001048</idno><idno type="wicri:Area/Main/Exploration">001048</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Systematic Comparison of Sets
of <sup>13</sup>C NMR
Spectra That Are Potentially Identical. Confirmation of the Configuration
of a Cuticular Hydrocarbon from the Cane Beetle <italic>Antitrogus
parvulus</italic></title><author><name sortKey="Basar, Norazah" sort="Basar, Norazah" uniqKey="Basar N" first="Norazah" last="Basar">Norazah Basar</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry, Faculty of Science,<institution>Universiti Teknologi Malaysia</institution>, Skudai, 81310 Johor,<country>Malaysia</country></nlm:aff><country xml:lang="fr">Malaisie</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Damodaran, Krishnan" sort="Damodaran, Krishnan" uniqKey="Damodaran K" first="Krishnan" last="Damodaran">Krishnan Damodaran</name><affiliation wicri:level="1"><nlm:aff id="aff2">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Liu, Hao" sort="Liu, Hao" uniqKey="Liu H" first="Hao" last="Liu">Hao Liu</name><affiliation wicri:level="1"><nlm:aff id="aff3">School of Chemistry,<institution>University of Manchester</institution>, Manchester M13 9PL,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Morris, Gareth X0a A" sort="Morris, Gareth X0a A" uniqKey="Morris G" first="Gareth X0a A." last="Morris">Gareth X0a A. Morris</name><affiliation wicri:level="1"><nlm:aff id="aff3">School of Chemistry,<institution>University of Manchester</institution>, Manchester M13 9PL,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Sirat, Hasnah M" sort="Sirat, Hasnah M" uniqKey="Sirat H" first="Hasnah M." last="Sirat">Hasnah M. Sirat</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Chemistry, Faculty of Science,<institution>Universiti Teknologi Malaysia</institution>, Skudai, 81310 Johor,<country>Malaysia</country></nlm:aff><country xml:lang="fr">Malaisie</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Thomas, Eric J" sort="Thomas, Eric J" uniqKey="Thomas E" first="Eric J." last="Thomas">Eric J. Thomas</name><affiliation wicri:level="1"><nlm:aff id="aff3">School of Chemistry,<institution>University of Manchester</institution>, Manchester M13 9PL,<country>United Kingdom</country></nlm:aff><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Curran, Dennis P" sort="Curran, Dennis P" uniqKey="Curran D" first="Dennis P." last="Curran">Dennis P. Curran</name><affiliation wicri:level="1"><nlm:aff id="aff2">Department of Chemistry,<institution>University of Pittsburgh</institution>, Pittsburgh, Pennsylvania 15260,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">The Journal of Organic Chemistry</title><idno type="ISSN">0022-3263</idno><idno type="eISSN">1520-6904</idno><imprint><date when="2014">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="jo-2014-012027_0010" id="ab-tgr1"></graphic></p><p>A systematic process is introduced
to compare <sup>13</sup>C NMR
spectra of two (or more) candidate samples of known structure to a
natural product sample of unknown structure. The process is designed
for the case where the spectra involved can reasonably be expected
to be very similar, perhaps even identical. It is first validated
by using published <sup>13</sup>C NMR data sets for the natural product
4,6,8,10,16,18-hexamethyldocosane. Then the stereoselective total
syntheses of two candidate isomers of the related 4,6,8,10,16-pentamethyldocosane
natural product are described, and the process is applied to confidently
assign the configuration of the natural product as (4<italic>S</italic>,6<italic>R</italic>,8<italic>R</italic>,10<italic>S</italic>,16<italic>S</italic>). This is accomplished even though the chemical shift
differences between this isomer and its (16<italic>R</italic>)-epimer
are only ±5–10 ppb (±0.005–0.01 ppm).</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Chow, S" uniqKey="Chow S">S. Chow</name></author><author><name sortKey="Fletcher, M T" uniqKey="Fletcher M">M. T. Fletcher</name></author><author><name sortKey="Lambert, L K" uniqKey="Lambert L">L. K. Lambert</name></author><author><name sortKey="Gallagher, O P" uniqKey="Gallagher O">O. P. Gallagher</name></author><author><name sortKey="Moore, C J" uniqKey="Moore C">C. J. Moore</name></author><author><name sortKey="Cribb, B W" uniqKey="Cribb B">B. W. Cribb</name></author><author><name sortKey="Allsopp, P G" uniqKey="Allsopp P">P. G. Allsopp</name></author><author><name sortKey="Kitching, W" uniqKey="Kitching W">W. Kitching</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Herber, C" uniqKey="Herber C">C. Herber</name></author><author><name sortKey="Breit, B" uniqKey="Breit B">B. Breit</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Basar, N B" uniqKey="Basar N">N. B. Basar</name></author><author><name sortKey="Liu, H" uniqKey="Liu H">H. Liu</name></author><author><name sortKey="Negi, D" uniqKey="Negi D">D. Negi</name></author><author><name sortKey="Sirat, H M" uniqKey="Sirat H">H. M. Sirat</name></author><author><name sortKey="Morris, G A" uniqKey="Morris G">G. A. Morris</name></author><author><name sortKey="Thomas, E J" uniqKey="Thomas E">E. J. Thomas</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Fletcher, C J" uniqKey="Fletcher C">C. J. Fletcher</name></author><author><name sortKey="Wheelhouse, K M P" uniqKey="Wheelhouse K">K. M. P. Wheelhouse</name></author><author><name sortKey="Aggarwal, V K" uniqKey="Aggarwal V">V. K. Aggarwal</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kobayashi, Y" uniqKey="Kobayashi Y">Y. Kobayashi</name></author><author><name sortKey="Czechtizky, W" uniqKey="Czechtizky W">W. Czechtizky</name></author><author><name sortKey="Kishi, Y" uniqKey="Kishi Y">Y. Kishi</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="De Haan, J W" uniqKey="De Haan J">J. W. de Haan</name></author><author><name sortKey="Van De Ven, L J M" uniqKey="Van De Ven L">L. J. M. van de Ven</name></author><author><name sortKey="Wilson, A R N" uniqKey="Wilson A">A. R. N. Wilson</name></author><author><name sortKey="Van X0a Der Hout Lodder, A E" uniqKey="Van X0a Der Hout Lodder A">A. E. van
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Zarbin</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>Malaisie</li><li>Royaume-Uni</li><li>États-Unis</li></country></list><tree><country name="Malaisie"><noRegion><name sortKey="Basar, Norazah" sort="Basar, Norazah" uniqKey="Basar N" first="Norazah" last="Basar">Norazah Basar</name></noRegion><name sortKey="Sirat, Hasnah M" sort="Sirat, Hasnah M" uniqKey="Sirat H" first="Hasnah M." last="Sirat">Hasnah M. Sirat</name></country><country name="États-Unis"><noRegion><name sortKey="Damodaran, Krishnan" sort="Damodaran, Krishnan" uniqKey="Damodaran K" first="Krishnan" last="Damodaran">Krishnan Damodaran</name></noRegion><name sortKey="Curran, Dennis P" sort="Curran, Dennis P" uniqKey="Curran D" first="Dennis P." last="Curran">Dennis P. Curran</name></country><country name="Royaume-Uni"><noRegion><name sortKey="Liu, Hao" sort="Liu, Hao" uniqKey="Liu H" first="Hao" last="Liu">Hao Liu</name></noRegion><name sortKey="Morris, Gareth X0a A" sort="Morris, Gareth X0a A" uniqKey="Morris G" first="Gareth X0a A." last="Morris">Gareth X0a A. Morris</name><name sortKey="Thomas, Eric J" sort="Thomas, Eric J" uniqKey="Thomas E" first="Eric J." last="Thomas">Eric J. Thomas</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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