Introduction of the new dipeptide isostere 7-endo-BtA as reverse turn inducer in a Bowman-Birk proteinase inhibitor:: Synthesis and conformational analysis

被引：16

作者：

Scarpi, D

Occhiato, EG

Trabocchi, A

Leatherbarrow, RJ

Brauer, ABE

Nievo, M

Guarna, A

机构：

[1] Univ Florence, Dipartimento Chim Organ U Schiff, I-50121 Florence, Italy

[2] Univ Florence, CNR, I-50121 Florence, Italy

[3] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AY, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2001年 / 9卷 / 06期

关键词：

D O I：

10.1016/S0968-0896(01)00046-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Two dipeptide isosteres 7-exo-BTG (1) and 7-endo-BtA (2), belonging to the new class of y/delta -bicyclic amino acid BTAa, were inserted into an 1 I-residue peptide deriving from the Bowman Birk Inhibitor (BBI) class of serine protease inhibitors, and the conformational properties of these modified peptides have been studied by NMR and molecular modelling. The dipeptide isostere 7-endo-BtA [(1R,4S,5R,7R)-4-endo-methyl-6,8-dioxa-3-azabicyclo[3.3.1]octane-7-endo-carboxylic acid] (2), derived from L-alanine and meso tartaric acid, gave rise to the modified BBI peptide 5 whose structure was very similar to that of the original peptide 3, suggesting a possible reverse turn inducing property for this dipeptide isostere. (C) 2001 Elsevier Science Ltd. All rights reserved.

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页码：1625 / 1632

页数：8

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