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dc.contributor.authorKomarov, Igor V
dc.contributor.authorYanik, Stanislav
dc.contributor.authorIshchenko, Aleksandr Yu
dc.contributor.authorDavies, John E
dc.contributor.authorGoodman, Jonathan M
dc.contributor.authorKirby, Anthony J
dc.date.accessioned2015-03-10T11:48:29Z
dc.date.available2015-03-10T11:48:29Z
dc.date.issued2015-01-21
dc.identifier.citationJournal of American Chemical Society, 2015, 137 (2), pp 926–930 DOI: 10.1021/ja511460a
dc.identifier.issn0002-7863
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/246951
dc.description.abstract1-Azatricyclo[3.3.1.1(3,7)]decan-2-one (3), the parent compound of a rare class of 90°-twisted amides, has finally been synthesized, using an unprecedented transformation. These compounds are of special interest as transition-state mimics for the enzyme-catalyzed cis-trans rotamer interconversion of amides involved in peptide and protein folding and function. The stabilization of the amide group in its high energy, perpendicular conformation common to both systems is shown for the rigid tricyclic system to depend, as predicted by calculation, on its methyl group substitution pattern, making 3 by some way the most reactive known "amide".
dc.description.sponsorshipFinancial assistance from Enamine Ltd. (www.enamine.net) is gratefully acknowledged. We also thank Dr. V. Stepanenko for valuable advice and encouragement which helped to find the nonstandard solutions to the synthetic problems, and Vitaliy Bilenko for drawing our attention to the instructive EI mass spectrum of compound 8.
dc.languageEnglish
dc.language.isoen
dc.publisherAmerican Chemical Society (ACS)
dc.rightsAttribution 2.0 UK: England & Wales
dc.rights.urihttp://creativecommons.org/licenses/by/2.0/uk/
dc.titleThe most reactive amide as a transition-state mimic for cis-trans interconversion.
dc.typeArticle
dc.description.versionThis is the final published version of the article, originally published in the Journal of the American Chemical Society, 2015, 137 (2), pp 926–93, DOI: 10.1021/ja511460a
prism.endingPage930
prism.publicationDate2014
prism.publicationNameJ Am Chem Soc
prism.startingPage926
prism.volume2
rioxxterms.versionofrecord10.1021/ja511460a
rioxxterms.licenseref.urihttp://www.rioxx.net/licenses/all-rights-reserved
rioxxterms.licenseref.startdate2014-12-22
dc.contributor.orcidGoodman, Jonathan [0000-0002-8693-9136]
dc.identifier.eissn1520-5126
rioxxterms.typeJournal Article/Review
cam.issuedOnline2015-01-09


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Attribution 2.0 UK: England & Wales
Except where otherwise noted, this item's licence is described as Attribution 2.0 UK: England & Wales