Preparation of 2S-(—)-4-Amino-2-Hydroxybutanoic Acid via Yeast-Catalyzed Stereoselective Reduction |
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Authors: | Keith J. Harris Charles J. Sih |
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Affiliation: | a School of Pharmacy, University of Wisconsin, Madison, WI, USA |
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Abstract: | The unusual amino acid S2-(—)-4-amino-2-hydroxybutanoic acid (S-AHBA) (1), a structural component of the antibiotic Amikacin, has been prepared via yeast-catalyzed stereoselective reduction of methyl-4-benzyloxycarbonyloxyamino-2-oxobutanoate (5). The most suitable yeast was found to be Saccharomyces carlsbergensis ATCC2345 and Saccharomyces sp. Edme, which gave 40% and 54% yield, respectively, of (S)-(+)-6 (88% ee). |
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Keywords: | Yeast stereoselective reduction 2S-(-)-4-amino-2-hydroxybutanoic acid bakers' yeast Amikacin |
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