Approaches to Cyclic Peptide beeta Turn Mimics

Authors: MacDonald M.; Aube J.

Source: Current Organic Chemistry, Volume 5, Number 4, April 2001 , pp. 417-438(22)

Publisher: Bentham Science Publishers

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Abstract:

The beeta-turn is a common recognition feature between peptide ligands and their macromolecular targets. The cyclization of a short peptide segment with a linker is one method of imitating this conformation. The first part of this review discusses tethering strategies which have resulted in the development of mimetics for the enkephalins and somatostatin as well as in the discovery of antagonists for targets such as thrombin, the CD4 protein on T lymphocytes, the integrins, and other receptors involved in inflammatory diseases. The second portion of this review describes the application of e-aminocaproic acid (Aca) as a tether in cyclic peptide beeta-turn mimics. Alkyl substituents on Aca may influence the b-turn preference of the dipeptide. The synthesis of the substituted Aca linkers and their incorporation into the macrocycles is highlighted.

Keywords: Cyclic Peptide; PEPTIDE MACROCYCLES; Cyclic Peptides; Tripeptides; THE ACA TETHER; Dimethyl Aca

Language: English

Document Type: Review article

DOI: http://dx.doi.org/10.2174/1385272013375517

Publication date: 2001-04-01