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

Abstract

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 CDCl(3) was also established. The compound is found to associate as an H-bonded carboxylic acid "dimer" in CDCl(3) solution, and VCD calculations on a model dimer fragment were required to establish the absolute configuration.

• Authors: Teresa B Freedman, Xiaolin Cao, Linda M Phillips, Peter T W Cheng, Richard Dalterio, Yue-Zhong Shu, Hao Zhang, Ning Zhao, Rajesh B Shukla, Adrienne Tymiak, Stephen K Gozo, Laurence A Nafie, Jack Z Gougoutas
• Journal: Chirality (Chirality) Vol. 18 Issue 9 Pg. 746-53 (Sep 2006) ISSN: 0899-0042 [Print] United States
• PMID: 16856170 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Acids
• Pyrrolidines
• Solutions
• pyrrolidine

Topics

• Acids (analysis, chemistry)
• Circular Dichroism (methods)
• Dimerization
• Models, Molecular
• Molecular Conformation
• Molecular Structure
• Pyrrolidines (analysis, chemistry)
• Solutions (chemistry)
• Spectrophotometry, Infrared
• Stereoisomerism