Regioselective Hydrolysis of Carbohydrate Secondary Acyl Esters By Lipases1
- 1 July 1989
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 8 (3) , 333-341
- https://doi.org/10.1080/07328308908048563
Abstract
Treatment of 1, 6-anhydro-2, 3, 4-tri-O-n-butanoyl-β-D-glucopyranose (3) with lipase preparations of Pseudomonas sp., Mucor miehei or Chromobacterium viscosum in aqueous media resulted in regioselective removal of the acylester at C-4 to afford 1, 6-anhydro-2, 3-di-O-n-butanoyl-β-D-glucopyranose (5). The C-2 acylester of compound 5 was efficiently removed with lipase of Candida cylindracea to give 1, 6-anhydro-3-O-n-butanoyl-β-D-glucopyranose (6). For 1, 6-anhydro-2, 3, 4-tri-O-n-butanoyl-β-D-galactopyranose (4) a different pattern of enzymatic hydrolysis was observed, indicating that the stereochemistry at C-4 is important for enzymatic hydrolysis.This publication has 6 references indexed in Scilit:
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