Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism

被引：18

作者：

Freedman, Teresa B. ^{[1
]}

Cao, Xiaolin

Phillips, Linda M.

Cheng, Peter T. W.

Dalterio, Richard

Shu, Yue-Zhong

Zhang, Hao

Zhao, Ning

Shukla, Rajesh B.

Tymiak, Adrienne

Gozo, Stephen K.

Nafie, Laurence A.

Gougoutas, Jack Z.

机构：

[1] Syracuse Univ, Dept Chem, Ctr Sci & Technol 1014, Syracuse, NY 13244 USA

[2] Bristol Myers Squibb Pharmaceut Res Inst, Analyt R&D, Princeton, NJ USA

[3] Bristol Myers Squibb Pharmaceut Res Inst, Hopewell, NJ USA

来源：

CHIRALITY | 2006年 / 18卷 / 09期

关键词：

vibrational circular dichroism; absolute configuration; solution conformation; acid dimer;

D O I：

10.1002/chir.20316

中图分类号：

R914 [药物化学];

学科分类号：

100701 [药物化学];

摘要：

Compound A, a novel disubstituted pyrrolidine acid, is a member of a new class of agents that are potentially useful for the treatment of diabetes and dyslipidemia. The absolute configuration of this compound was determined by using vibrational circular dichroism (VCD). The results are in agreement with the assignments based on both X-ray analysis and the stereo-selective chemical synthesis. During VCD analysis, the solution conformation for a portion of compound A in CDCl3 was also established. The compound is found to associate as an H-bonded carboxylic acid "dimee' in CDCl3 solution, and VCD calculations on a model dimer fragment were required to establish the absolute configuration.

引用

页码：746 / 753

页数：8

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