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The ethylene group as a peptide bond mimicking unit: A theoretical conformational analysis

✍ Scribed by Maciej Bagińki; Lucjan Piela; Jeffrey Skolnick

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
720 KB
Volume
14
Category
Article
ISSN
0192-8651

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✦ Synopsis

One of the features of the polypeptide backbone is that it represents a flexible chain that contains almost rigid CO-NH peptide bonds. One may try to substitute one or more such bonds by another relatively rigid unit to maintain the overall conformational properties of the backbone and at the same time modify some other properties of the molecule ("pseudopeptide"), such as the ability to form hydrogen bonds. By a detailed conformational analysis, it is shown that the carbon-carbon double bond is quite isosteric with the peptide bond and for this reason suitable for such a substitution. This is accomplished by applying molecular mechanics in calculation of the 4, $ maps for pseudopeptide analogs of the N-acetyl-Ala-NHMe molecule.

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