Backbone cyclization: A new method for conferring conformational constraint on peptides

Chaim Gilon, David Halle, Michael Chorev, Zvi Selincer, Gerardo Byk

Research output: Contribution to journalArticlepeer-review

197 Scopus citations

Abstract

This article describes a new concept of medium‐ and long‐range cyclization of peptides through “backbone cyclization.” In this approach, conformational constraints are conferred on a peptide by linking ω‐substituted alkylidene chains replacing Nα or Cα hydrogens in a peptidic backbone. Backbone cyclization, which is divided into N‐backbone and C‐backbone cyclizations, allow for new modes of cyclization in addition to the classical ones that are limited to cyclization through the side chains and/or the amino or carboxyl terminal groups. The article also describes the application of the N‐backbone cyclization to the active region of substance P. Conformational constraints of this peptide by the classical cyclization modes led to inactive analogues whereas N‐backbone cyclization provided an active, selective, and metabolically stable analogue.

Original languageEnglish
Pages (from-to)745-750
Number of pages6
JournalBiopolymers
Volume31
Issue number6
DOIs
StatePublished - May 1991
Externally publishedYes

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