A systematic study of the solid state and solution phase conformational preferences of β-peptides derived from C(3)-alkyl substituted transpentacin derivatives

被引：21

作者：

Abraham, Elin ^{[1
]}

Claridge, Timothy D. W. ^{[1
]}

Davies, Stephen G. ^{[1
]}

Odell, Barbara ^{[1
]}

Roberts, Paul M. ^{[1
]}

Russell, Angela J. ^{[1
]}

Smith, Andrew D. ^{[1
]}

Smith, Lorna J. ^{[2
]}

Storr, Helen R. ^{[1
]}

Sweet, Miles J. ^{[1
]}

Thompson, Amber L. ^{[1
]}

Thomson, James E. ^{[1
]}

Tranter, George E. ^{[1
,3
]}

Watkin, David J. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Oxford, Inorgan Chem Lab, Dept Chem, Oxford OX1 3QR, England

[3] Oxford Univ Begbroke Sci Pk, Chiralabs Ltd, BCIE, Yarnton OX5 1PF, Oxon, England

来源：

TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 01期

关键词：

PARALLEL KINETIC RESOLUTION; ASYMMETRIC-SYNTHESIS; ACID; 3-ALKYL-CISPENTACIN; OLIGOMERS;

D O I：

10.1016/j.tetasy.2010.12.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The solid state and solution phase conformational preferences of a homologous series of beta-peptides derived from a range of 2-amino-3-alkylcyclopentanecarboxylic acid residues have been investigated using a variety of spectroscopic and crystallographic techniques. These studies indicate that C(3)-alkyl substitution trans to the amino group on the cyclopentane backbone is tolerated by the established 12-helix secondary structural preference of the parent pentamer and hexamer derived from 2-aminocyclopentanecarboxylic acid (transpentacin) residues in both the solid state and solution phase. Evidence for the alternative turn type conformation identified for the C(3)-unsubstituted tetramer was not observed in the C(3)-alkyl substituted derivatives, consistent with the alkyl substituent anti to the amino functionality destabilising this motif. These results suggest that oligomers based around the transpentacin scaffold may be amenable to further elaboration at C(3) anti to the amino group with retention of the secondary structure. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：69 / 100

页数：32

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