The most reactive amide as a transition-state mimic for cis-trans interconversion.
Authors
Komarov, Igor V
Yanik, Stanislav
Ishchenko, Aleksandr Yu
Davies, John
Kirby, Tony
Publication Date
2015-01-21Journal Title
J Am Chem Soc
ISSN
0002-7863
Publisher
American Chemical Society (ACS)
Volume
2
Pages
926-930
Language
English
Type
Article
Metadata
Show full item recordCitation
Komarov, I. V., Yanik, S., Ishchenko, A. Y., Davies, J., Goodman, J., & Kirby, T. (2015). The most reactive amide as a transition-state mimic for cis-trans interconversion.. J Am Chem Soc, 2 926-930. https://doi.org/10.1021/ja511460a
Abstract
1-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".
Sponsorship
Financial 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.
Identifiers
External DOI: https://doi.org/10.1021/ja511460a
This record's URL: https://www.repository.cam.ac.uk/handle/1810/246951
Rights
Attribution 2.0 UK: England & Wales
Licence URL: http://creativecommons.org/licenses/by/2.0/uk/
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