An Evaluation of Peptide-bond Isosteres

Overview

Journal Chembiochem

Specialty Biochemistry

Date 2011 Jul 14

PMID 21751326

Citations 64

Authors

Amit Choudhary

Ronald T Raines

Affiliations

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Abstract

Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partake in noncovalent interactions is compared with that of the peptide bond. The consequential perturbations provide a useful tool for chemical biologists to reveal new structure-function relationships, and to endow peptides and proteins with desirable attributes.

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