期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 4, 页码 1658-1662出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo802495f
关键词
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资金
- Knowledge Innovation Program [KSCX 2-YW-G-031]
- DARPA [HR0011-06-1-0032]
- Robert A. Welch Foundation [N-118]
Use of isolated carbonyl reductases in the reduction of aromatic beta-ketonitriles have completely eliminated the competing alpha-ethylation, which is often observed with whole cell biocatalysts. By choosing suitable recombinant carbonyl reductase, the reduction of beta-ketonitriles afforded (R)- or (S)-beta-hydroxy nitrites with excellent optical purity and yield. Subsequently, nitrilase-catalyzed hydrolysis of the obtained optically pure beta-hydroxy nitrites led to the corresponding beta-hydroxy carboxylic acids in high yields. More importantly, the sequential enzymatic reduction and hydrolysis could be carried out in two-step-one-pot fashion without the isolation of intermediates alpha-hydroxy nitrites, lowering the cost and minimizing the environmental impact. This allows ready access to both antipodes of chiral beta-hydroxy nitrites and beta-hydroxy carboxylic acids of pharmaceutical importance with excellent optical purity.
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