title: 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.affiliation: Department of Chemistry, Syracuse University, Syracuse, New York 13244, USA. jack.gougoutas@bms.com
authors.forename: Teresa B
authors.initials: TB
authors.lastname: Freedman
authors.forename: Xiaolin
authors.initials: X
authors.lastname: Cao
authors.forename: Linda M
authors.initials: LM
authors.lastname: Phillips
authors.forename: Peter T W
authors.initials: PT
authors.lastname: Cheng
authors.forename: Richard
authors.initials: R
authors.lastname: Dalterio
authors.forename: Yue-Zhong
authors.initials: YZ
authors.lastname: Shu
authors.forename: Hao
authors.initials: H
authors.lastname: Zhang
authors.forename: Ning
authors.initials: N
authors.lastname: Zhao
authors.forename: Rajesh B
authors.initials: RB
authors.lastname: Shukla
authors.forename: Adrienne
authors.initials: A
authors.lastname: Tymiak
authors.forename: Stephen K
authors.initials: SK
authors.lastname: Gozo
authors.forename: Laurence A
authors.initials: LA
authors.lastname: Nafie
authors.forename: Jack Z
authors.initials: JZ
authors.lastname: Gougoutas
mesh_terms: D000143:Acids / Q000032:analysis* / Q000737:chemistry*; D002942:Circular Dichroism / Q000379:methods*; D019281:Dimerization; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011759:Pyrrolidines / Q000032:analysis* / Q000737:chemistry*; D012996:Solutions / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
chemical_list: D000143:Acids; D011759:Pyrrolidines; D012996:Solutions; C032519:pyrrolidine