Poly-L-proline type II peptide mimics based on the 3-azabicyclo[3.1.0]hexane system

被引：29

作者：

Mamai, A ^{[1
]}

Zhang, R ^{[1
]}

Natarajan, A ^{[1
]}

Madalengoitia, JS ^{[1
]}

机构：

[1] Univ Vermont, Dept Chem, Burlington, VT 05405 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 02期

关键词：

D O I：

10.1021/jo001201o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper describes conformational studies of proline-templated amino acids (PTAAs) based on the 3-azabicyclol[3.1.0]hexane system as well as conformational studies on short peptides composed of these PTAAs. NOE data, coupling constants, and molecular modeling are consistent with a flattened boat conformation for monomeric and oligomeric residues based on this bicyclic system. NMR studies on dimeric and trimeric oligomers are consistent with a populated poly-L-proline type II conformation in CDCl3 and D2O. Solution studies and molecular modeling predicts phi similar to -70 degrees, psi similar to 131 degrees, chi1 similar to -57 degrees, and chi2 similar to -158 degrees for oligomeric residues.

引用

页码：455 / 460

页数：6

共 26 条

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