Please use this identifier to cite or link to this item: https://doi.org/10.1021/cs200099k
Title: Regio- and stereoselective concurrent oxidations with whole cell biocatalyst: Simple and green syntheses of enantiopure 1,2-diols via oxidative kinetic resolution
Authors: Jia, X.
Xu, Y. 
Li, Z. 
Keywords: 2-diols
concurrent oxidations
enantiopure 1
enantioselective synthesis
enzyme catalysis
Sphingomonas sp. HXN- 200
tandem biocatalysis
Issue Date: 3-Jun-2011
Source: Jia, X., Xu, Y., Li, Z. (2011-06-03). Regio- and stereoselective concurrent oxidations with whole cell biocatalyst: Simple and green syntheses of enantiopure 1,2-diols via oxidative kinetic resolution. ACS Catalysis 1 (6) : 591-596. ScholarBank@NUS Repository. https://doi.org/10.1021/cs200099k
Abstract: A simple and green method for preparing several enantiopure 1,2-diols was developed, for the first time, via regio- and stereoselective concurrent oxidations of the racemates with microbial cells. Sphingomonas sp. HXN-200 was found to catalyze the regio- and stereoselective oxidations of 3-O-benzylglycerol 1 to the corresponding '-hydroxy aldehyde 5 and then to the '-hydroxy carboxylic acid 6. Concurrent biooxidations of racemic 3-O-benzylglycerol 1 with resting cells of Sphingomonas sp. HXN-200 gave (S)-1 in 99.2% enantiomeric excess (ee) and 32% yield. Similar biooxidations of racemic 1-(4-chlorophenyl)-1,2-ethanediol 2, 1-(4-methylphenyl)-1,2-ethanediol 3, and phenyl-1,2-ethanediol 4 gave (R)-2 in 98.4% ee and 48% yield, (R)-3 in 99.6% ee and 45% yield, and (R)-4 in 98.7% ee and 36% yield, respectively. These represent the best results known thus far for the enzymatic syntheses of the useful and valuable diols (S)-1 and (R)-2-4. © 2011 American Chemical Society.
Source Title: ACS Catalysis
URI: http://scholarbank.nus.edu.sg/handle/10635/64503
ISSN: 21555435
DOI: 10.1021/cs200099k
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

12
checked on Dec 6, 2017

WEB OF SCIENCETM
Citations

12
checked on Nov 22, 2017

Page view(s)

32
checked on Dec 10, 2017

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.