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  • Title: Determination of the absolute configuration and solution conformation of a novel disubstituted pyrrolidine acid A by vibrational circular dichroism.
    Author: Freedman TB, Cao X, Phillips LM, Cheng PT, Dalterio R, Shu YZ, Zhang H, Zhao N, Shukla RB, Tymiak A, Gozo SK, Nafie LA, Gougoutas JZ.
    Journal: Chirality; 2006 Sep; 18(9):746-53. PubMed ID: 16856170.
    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.
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