Stereospecific Biohydroxylations of Protected Carboxylic Acids with Cunninghamella blakesleeana.

Applied and Environmental Microbiology
M KreinerA Zeiser

Abstract

Cunninghamella blakesleeana DSM 1906 was found to be an efficient biocatalyst for the biotransformation of cycloalkylcarboxylic acids into hydroxy and oxo derivatives. When cultivated in submerged culture, the fungus grew in pellets. In comparison with malt extract-glucose-peptone-yeast extract medium (medium E), Czapek-Dox medium was found to reduce pellet size. Cycloalkylcarboxylic acids were protected against microbial degradation by chemical transformation into 2-cycloalkyl-1,3-benzoxazoles. The transformations of protected cyclopentyl-, cyclohexyl-, cycloheptyl-, and cyclooctylcarboxylic acids by C. blakesleeana were investigated. The biotransformations were performed in medium E by using an aerated, stirred-tank bioreactor. The transformation of 2-cyclopentyl-1,3-benzoxazole yielded (1S,3S)-3-(benz-1,3-oxazol-2-yl)cyclopentan-1-ol as the main product. The main by-product was (1R)-3-(benz-1,3-oxazol-2-yl)cyclopentan-1-one, and 2-(benz-1,3-oxazol-2-yl)cyclopentan-1-ol was also obtained in small amounts. During the experiment, the enantiomeric excess of the main product increased up to 64%. 2-Cyclohexyl-1,3-benzoxazole was hydroxylated to 4-(benz-1,3-oxazol-2-yl)cyclohexan-1-ol. 2-Cycloheptyl-1,3-benzoxazole and 2-cyclooctyl...Continue Reading

References

Jan 1, 1979·Advances in Applied Microbiology·J P Rosazza, R V Smith
Mar 1, 1992·Applied and Environmental Microbiology·J V PothuluriC E Cerniglia
Nov 1, 1985·Archives of Microbiology·C E CernigliaR H Heflich

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Citations

Feb 24, 2001·Chemistry : a European Journal·A de RaadtH Weber
Jan 28, 2012·Indian Journal of Microbiology·Gurram Shyam PrasadS M Reddy

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