Bicyclic Peptides As Type I/Type Ii Beta-Turn Scaffolds(599 views) Lombardi A, D'Auria G, Saviano M, Maglio O, Nastri F, Quartara L, Pedone C, Pavone V
Affiliations: CIRPB, CEINGE-Biotecnologie Avanzate, Ctro. Studio Biocristallografia-CNR, Via Mezzocannone 4, I-80134 Napoli, Italy
References: Not available.
Bicyclic Peptides As Type I/Type Ii Beta-Turn Scaffolds
We recently reported the rational design, synthesis, and structural characterization of the most potent and selective peptide-based neurokinin A antagonist thus far described: cyclo (Met (1) -Asp (2) -Trp (3) -Phe (4) -Dap (5) -Leu (6)) cyclo (2 beta-5 beta). Its bicyclic structure is characterized by a type I and a type II two beta-turn around Trp (3) -Phe (4) and Leu (6) -Met (1), respectively. In order to understand whether the two different beta-turned structures are determined by the bicyclic structure or by the amino acid type at the corner positions, we have synthesized the pseudo-symmetrical analogue cyclo (Phe (1) -Asp (2) -Trp (3) -Phe (4) -Dap (5) -Trp (6)) cyclo (2 beta-5 beta). The structural characterization in the crystal state and in solution, here reported, gives an experimental evidence that the backbone of the bicyclic structure is a rigid scaffold that can be used to build both a type I and type II beta-turn independently from the amino acid composition. (C) 1997 John Wiley & Sons, Inc
Bicyclic Peptides As Type I/Type Ii Beta-Turn Scaffolds
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