Enzymatic Synthesis of Galactosylated 1d-Chiro-Inositol and 1d-Pinitol Derivatives Using the β-Galactosidase from Bacillus circulans

Joanne Hart; Andrew Falshaw; Erzsébet Farkas; Joachim Thiem

doi:10.1055/s-2001-11388

Synlett 2001; 2001(3): 0329-0332
DOI: 10.1055/s-2001-11388

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Enzymatic Synthesis of Galactosylated 1d-Chiro-Inositol and 1d-Pinitol Derivatives Using the β-Galactosidase from Bacillus circulans

Joanne Hart^* , Andrew Falshaw, Erzsébet Farkas, Joachim Thiem

^*Carbohydrate Chemistry Team, Industrial Research Ltd., PO Box 31-310, Lower Hutt, New Zealand; Fax + 49(0)4 04 28 38 43 25; E-mail: thiem@chemie.uni-hamburg.de

Abstract

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The β-d-galactosidase from Bacillus circulans regioselectively galactosylates 1d-chiro-inositol and 1d-pinitol (1d-3-O-methyl-chiro-inositol) to give mono- and digalactosylated inositols in yields of up to 45%. The enzyme does not galactosylate 1l-chiro-inositol or 1l-quebrachitol (1l-2-O-methyl-chiro-inositol). This is the first report of enzymatic glycosylation of chiro-inositol and its derivatives.

carbohydrates - enzymatic glycosylations - Bacillus circulans - β-d-galactosidase - inositol oligosaccharides

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