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Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism
Author(s) -
Freedman Teresa B.,
Cao Xiaolin,
Phillips Linda M.,
Cheng Peter T. W.,
Dalterio Richard,
Shu YueZhong,
Zhang Hao,
Zhao Ning,
Shukla Rajesh B.,
Tymiak Adrienne,
Gozo Stephen K.,
Nafie Laurence A.,
Gougoutas Jack Z.
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20316
Subject(s) - absolute configuration , chemistry , vibrational circular dichroism , pyrrolidine , dimer , circular dichroism , stereochemistry , crystallography , organic chemistry
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. Chirality, 2006. © 2006 Wiley‐Liss, Inc.