Regioselective deacetylation of peracetylated monosaccharide derivatives by polyethylene glycol-modified lipase for the oligosaccharide synthesis |
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Authors: | Yoh Kodera Katsukiyo Sakurai Yuiko Satoh Takeshi Uemura Yuji Kaneda Hiroyuki Nishimura Misao Hiroto Ayako Matsushima Yuji Inada |
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Affiliation: | (1) Toin Human Science and Technology Center, Department of Materials Science and Technology, Toin University of Yokohama, Aoba-ku Yokohama, Japan;(2) The Tokyo Research Institute, Seikagaku Corporation, Higashiyamato Tokyo, Japan |
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Abstract: | Lipase modified with polyethylene glycol became soluble and active in organic solvents, and catalyzed regioselective deacetylation of peracetylated monosaccharide derivatives in 1,1,1-trichloroethane. The deacetylation occurred only at the positions of C-4 and C-6 of the glycopyranoside ring. Especially, peracetylated methyl -D-xylopyranoside and peracetylated L-serine--D-xylopyranoside were hydrolyzed only at the position of C-4. Subsequently, one of the resulting products, that is L-serine-2,3-di-O-acetyl--D-xylopyranoside, was coupled with galactose residue to obtain L-serine-4-O-(-D-galactopyranosyl)--D-xylopyranoside, a model compound of the carbohydrate-protein linkage region of proteoglycans. |
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