Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 4, Pages 1658-1662Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802495f
Keywords
-
Categories
Funding
- Knowledge Innovation Program [KSCX 2-YW-G-031]
- DARPA [HR0011-06-1-0032]
- Robert A. Welch Foundation [N-118]
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available