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Issue 12, 1991
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(3S)-3-hydroxyquinidine, the major biotransformation product of quinidine. Synthesis and conformational studies. X-Ray molecular structure of (3S)-3-hydroxyquinidine methanesuiphonate

Abstract

(3S)-3-Hydroxyquinidine, the major metabolite of the Cinchona alkaloid quinidine, was prepared by synthetic chemical modification or microbial oxidation of quinidine. The structure of this metabolite has been demonstrated to be (3S)-3-hydroxyquinidine by 1H and 13C NMR, IR, UV and mass spectral analysis. Previously published comparisons of the 13C NMR spectra of 3-hydroxyquinidine and model compounds were used to establish the absolute stereochemistry of the metabolite (see ref. 8). This assignment has been verified by single-crystal X-ray analysis of (3S)-3-hydroxyquinidine methanesulphonate. The gas- and solution-phase conformational preference of the metabolite derived from molecular modelling and NOE studies are compared with the conformation observed by X-ray crystallography.

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Article type: Paper
DOI: 10.1039/P19910003017
Citation: J. Chem. Soc., Perkin Trans. 1, 1991, 3017-3026
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    (3S)-3-hydroxyquinidine, the major biotransformation product of quinidine. Synthesis and conformational studies. X-Ray molecular structure of (3S)-3-hydroxyquinidine methanesuiphonate

    F. I. Carroll, P. Abraham, K. Gaetano, S. W. Mascarella, R. A. Wohl, J. Lind and K. Petzoldt, J. Chem. Soc., Perkin Trans. 1, 1991, 3017
    DOI: 10.1039/P19910003017

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