Regioselective enzymic deacetylation of octa-O-acetylsucrose: preparation of hepta-O-acetylsucroses.
Deacetylation of octa-O-acetylsucrose (1) with Alcalase or protease N gave the 2,3,4,6,3',4',6'-hepta-acetate (2) as the initial major product with the 2,3,4,6,3',4'-hexa-acetate (3) as the subsequent main product. The 2,3,4,1',3',4',6'-hepta-acetate (5) was obtained from 1 by the action of lipase OF or lipase AP6, and the 2,3,4,6,1',3',6'-(4) and 2,3,4,6,1',3',4'-hepta-acetate (7) by the action of Candida lipase and chymotrypsin, respectively. The 2,3,6,1',3',4',6'-hepta-acetate (6) was formed from 5 by acyl migration.
Chang
K Y
KY
Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan.
Wu
S H
SH
Wang
K T
KT
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D007202:Indicators and Reagents; D008049:Lipase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009904:Optical Rotation; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D000085:Acetates; D007202:Indicators and Reagents; C026879:sucrose octaacetate; D013395:Sucrose; D008049:Lipase