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|Title:||Regio- and stereoselective concurrent oxidations with whole cell biocatalyst: Simple and green syntheses of enantiopure 1,2-diols via oxidative kinetic resolution|
Sphingomonas sp. HXN- 200
|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.|
|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|
|Appears in Collections:||Staff Publications|
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