Regiospecific alkaline protease-catalyzed divinyl acyl transesterifications of primary hydroxyl groups of mono- and di-saccharides in pyridine.
This paper describes highly selective transesterification reactions, catalyzed by an alkaline protease from Bacillus subtilis in pyridine, of several mono- and di-saccharides with divinyl dicarboxylates ranging from 4 to 10 carbon atoms. A series of polymerizable vinyl fatty acid sugar esters were obtained with good selectivity and high yields. Most products had high proportions of the alpha anomer. The influences of the enzymes, solvents, temperature, and acyl donor chain length on the reaction were studied. Vinyl sugar esters offer a new family of functional water-soluble monomers for preparation of sugar-containing polymers.
Wu
Qi
Q
Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China.
Wang
Na
N
Xiao
Yong-Mei
YM
Lu
De-Shui
DS
Lin
Xian-Fu
XF
D001412:Bacillus subtilis / Q000201:enzymology; D001426:Bacterial Proteins / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D004187:Disaccharides / Q000737:chemistry*; D010450:Endopeptidases / Q000737:chemistry*; D004951:Esterification; D004952:Esters / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D001426:Bacterial Proteins; D004187:Disaccharides; D004952:Esters; D009005:Monosaccharides; D011725:Pyridines; D014753:Vinyl Compounds; D010450:Endopeptidases; C087822:alkaline protease; C023666:pyridine