✦ LIBER ✦
Substituent effects on the regioselectivity of enzymatic acylation of 6-O-alkylglycopyranosides using Pseudomonas cepacia lipase
✍ Scribed by David A. MacManus; Evgeny N. Vulfson
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 730 KB
- Volume
- 279
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The regioselectivity of acylation of a range of 6-O-protected glycosides using Pseudomonas cepacia lipase in vinyl acetate was investigated. In general, cY-glycosides were acylated at the O-2 position and P-glycosides were acylated at the O-3 position. The effects of varying the size/hydrophobicity of the O-6 and anomeric substituents on the regioselectivity of the reaction are discussed in terms of the binding of the substrate in the active site of the enzyme.