Esterase catalyzed regioselective hydrolyses of acetylated monosaccharides

• Published in: Tetrahedron Vol. 49; no. 47; pp. 10977 - 10986
• Main Authors: TOMIC, S, LJEVAKOVIC, D, TOMASIC, J
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 1993; Elsevier
• Subjects: Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Exact sciences and technology; Fundamental and applied biological sciences. Psychology; Methods. Procedures. Technologies; Organic chemistry; Preparations and properties; Aldose; Regioselectivity; Enzyme; Deacetylation; Aminoglycoside; Carbon Isotopes; Hydrolases; Esterases; Glycoside; Labelled compound; Enzymatic reaction
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(01)80251-9

Deacylations of fully acylated D-glucopyranoses, methyl D-glucopyranosides, 2-acetamido-2-deoxy- D-glucopyranoses glucopyranoses and methyl 2-acetamido-2-deoxy- D-glucopyranosides catalyzed by rabbit serum or the esterase isolated from rabbit serum were investigated. Depending on the structure of the acyl protecting group a high degree of regioselectivity is observed. Products of enzymic hydrolysis followed by intramolecular migrations of acetyl groups are also described. Regioselective deacylations of the presented fully acylated monosaccharides catalyzed by rabbit serum or the esterase isolated from rabbit serum were investigated. Intramolecular migration of acetyls in partially protected substrates was observed.