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Biotransformation of Tolbutamide to 4'-hydroxytolbutamide by the Fungus Cunninghamella Blakesleeana

Biotransformation of Tolbutamide to 4'-hydroxytolbutamide by the Fungus Cunninghamella Blakesleeana

Haihua Huang, Xiuwei Yang, Qiang Li, Lu Sun, Dafang Zhong

Appl Microbiol Biotechnol. 2006 Sep;72(3):486-91.

PMID: 16493553

Abstract:

The hypoglycemic drug tolbutamide is commonly used as a probe drug to evaluate CYP2C9 enzyme activity in terms of production of 4'-hydroxytolbutamide. In the present study, an initial screening of seven filamentous fungi was carried out to identify which was most competent to transform tolbutamide into 4'-hydroxytolbutamide. From this screening, the fungus Cunninghamella blakesleeana AS 3.910 was selected as a suitable bioconverter. At a concentration of 1.2 mg ml(-1), the growing fungus transformed 95.0% of tolbutamide into 4'-hydroxytolbutamide in 96 h. With resting culture, the yield could reach 91.7% and exceeded 91.0% even when the tolbutamide concentration was increased to 4.0 mg ml(-1). On scale-up to 3 l buffer containing 12.0 g tolbutamide, 90% of tolbutamide was transformed into 4'-hydroxytolbutamide in 96 h. Work-up of the broth by column chromatography and recrystallization yielded 6.5 g (53.9% recovered) of 4'-hydroxytolbutamide with a purity of more than 99%. These results suggest C. blakesleeana AS 3.910 is a useful biosynthetic tool in the preparation of 4'-hydroxytolbutamide.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP5719857	4-Hydroxytolbutamide		5719-85-7	Price

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