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Conformation-activity correlations for chemotactic tripeptide analogs incorporating dialkyl residues with linear and cyclic alkyl sidechains at position 2

Prasad, Sudhanand and Balaji Rao, R and Bergstrand, Hakan and Lundquist, Britta and Becker, Elmer L and Balaram, P (1996) Conformation-activity correlations for chemotactic tripeptide analogs incorporating dialkyl residues with linear and cyclic alkyl sidechains at position 2. In: International Journal Of Peptide And Protein Research, 48 (04). pp. 312-318.

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Abstract

Five stereochemically constrained analogs of the chemotactic tripeptide incorporating 1-aminocycloalkane-1-carboxylic acid (Ac(n)c) and alpha,alpha-dialkylglycines (Deg, diethylglycine; Dpg, n,n-dipropylglycine and Dbg, n,n-dibutylglycine) at position 2 have been synthesized. NMR studies of peptides For-Met-Xxx-Phe-OMe (Xxx = Ac(7)c, I; Ac(8)c, II; Deg, III; Dpg, IV and Dbg, V; For, formyl) establish that peptides with cycloalkyl residues, I and II, adopt folded beta-turn conformations in CDCl3 and (CD3)(2)SO. In contrast, analogs with linear alkyl sidechains, III-V, favour fully extended (C-5) conformations in solution. Peptides I-V exhibit high activity in inducing beta-glucosaminidase release from rabbit neutrophils, with ED(50) values ranging from 1.4-8.0 x 10(-11)M. In human neutrophils the Dxg peptides III-V have ED(50) values ranging from 2.3 x 10(-8) to 5.9 x 10(-10) M, with the activity order being V > IV > III. While peptides I-IV are less active than the parent. For-Met-Leu-Phe-OH, in stimulating histamine release from human basophils, the Dbg peptide V is appreciably more potent, suggesting its potential utility as a probe for formyl peptide receptors.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Munksgaard.
Keywords: chemotactic peptides;alpha,alpha-dialkylated residues; peptide conformation;beta-turns.
Department/Centre: Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited: 05 Mar 2009 09:02
Last Modified: 19 Sep 2010 05:27
URI: http://eprints.iisc.ernet.in/id/eprint/19249

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