Synthesis of acylated methyl - β- d-xylopyranosides and their enzymic deacylations by rabbit serum esterases

• Published in: Carbohydrate research Vol. 302; no. 1; pp. 13 - 18
• Main Authors: Petrovic, Tomic, S, Ljevakovic, D, Tomasic, J
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 11.07.1997; Elsevier
• Subjects: Acylation; Animals; Biochemistry & Molecular Biology; Chemistry; Chemistry, Applied; Chemistry, Organic; Enzymic deacylations; Esterases - blood; Esterases - metabolism; Hydrolysis; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Methyl β- d-xylopyranosides, acylated; Methylglycosides - chemical synthesis; Methylglycosides - metabolism; Pentanoic Acids - chemistry; Pentanoic Acids - metabolism; Physical Sciences; Rabbit serum esterases; Rabbits; Science & Technology; Methyl β- d-xylopyranosides, acylated; Enzymic deacylations; Rabbit serum esterases; ESTERIFICATIONS; MONOSACCHARIDES; HYDROLYZES; SELECTIVE PIVALOYLATION; ENZYMATIC DEACYLATIONS; enzymic deacylations; ESTERIFIED SACCHARIDES; SUGARS; methyl beta-D-xylopyranosides, acylated; rabbit serum esterases
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(97)00104-3

Selective pivaloylations of methyl β- d-xylopyranoside have been studied under various reaction conditions. Partially pivaloylated products were submitted to additional acetylations. The structures were established by 1H NMR spectroscopy. Representatives of acylated methyl ( β- d-xylopyranosides (acyl being pivaloyl, acetyl, or a combination of both) were submitted to hydrolysis catalyzed by rabbit serum and esterases isolated from rabbit serum.