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Lipase-catalysed Preparation of Acetates of 4-nitrophenyl beta-D-xylopyranoside and Their Use in Kinetic Studies of Acetyl Migration

Lipase-catalysed Preparation of Acetates of 4-nitrophenyl beta-D-xylopyranoside and Their Use in Kinetic Studies of Acetyl Migration

Mária Mastihubová, Peter Biely

Carbohydr Res. 2004 May 17;339(7):1353-60.

PMID: 15113674

Abstract:

Di-O-acetates and mono-O-acetates of 4-nitrophenyl beta-D-xylopyranoside were prepared by use of lipase PS-30. Polarity of organic solvents and reaction time affected the regioselectivity of the di-O-acetylation as well as the yields of monoacetates. The kinetics of acetyl groups migration in these derivatives was studied in aqueous media using HPLC. Migration of the acetyl group strongly depended on pH. The highest rate of acetyl migration was observed from O-2 to O-3 in both 2,4-di-O-acetate and 2-O-acetate. On the contrary, acetyl exchange between O-3 and O-4 in both directions was slower than between O-2 and O-3. The 2,3-di-O-acetate and 4-O-acetate showed to be the most stable towards acetyl migration. The 3,4-di-O-acetate and 4-O-acetate were dominant in the corresponding equilibration mixtures.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2001969	4-Nitrophenyl β-D-xylopyranoside		2001-96-9	Price

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