Chemoenzymatic synthesis of glycoconjugate polymers: greening the synthesis of biomaterials

被引：27

作者：

Miura, Y ^{[1
]}

Ikeda, T ^{[1
]}

Wada, N ^{[1
]}

Sato, H ^{[1
]}

Kobayashi, K ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan

来源：

GREEN CHEMISTRY | 2003年 / 5卷 / 05期

关键词：

D O I：

10.1039/b305294j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Glycoconjugate polymers with biodegradable poly(vinyl alcohol) (PVA) were synthesized via lipase-catalyzed transesterification of sugar alcohols (maltitol and lactitol) with divinyl dicarboxylates and subsequent radical polymerization. The conversion and chemoselectivity in transesterification were dependent on the lipases, the sugar alcohols, and the alkyl chain length of the dicarboxylates. Chemoselective esterification was attained in the presence of lipase from Candida antarctica (lipase CA) to give maltitol 6-vinyl sebacate, lactitol 6-vinyl sebacate, and lactitol 6-vinyl adipate in high yields. Polymerization of these vinyl esters with hydrogen peroxide/ascorbic acid as initiator gave glycoconjugate polymers. These polymers were suggested to take micellar conformations in water and to bind strongly to specific lectins (concanavalin A or RCA(120)). The biodegradabilities of these polymers were modest but higher than PVA. This simple synthesis will be useful to develop various glycoconjugate polymers with high biological activities due to the multivalent glyco-cluster effect and biodegradability due to their PVA backbone and ester linkage.

引用

页码：610 / 614

页数：5

共 18 条

[1] Recent developments in oligosaccharide synthesis [J].

Davis, BG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (14) :2137-2160

[2] Molecular design and biological potential of galacto-type trehalose as a nonnatural ligand of Shiga toxins [J].

Dohi, H ;

Nishida, Y ;

Furuta, Y ;

Uzawa, H ;

Yokoyama, S ;

Ito, S ;

Mori, H ;

Kobayashi, K .

ORGANIC LETTERS, 2002, 4 (03) :355-357

[3]

KILBANOV AM, 1986, CHEMTECH, V16, P354

[4]

Kitagawa M., 1997, CARBOHYDR LETT, V2, P343

[5]

KOBAYASHI A, 1986, MAKROMOL CHEM-RAPID, V7, P645

[6] PREPARATION OF MICROLATEX DISPERSIONS USING OIL-IN-WATER MICROEMULSIONS [J].

LARPENT, C ;

TADROS, TF .

COLLOID AND POLYMER SCIENCE, 1991, 269 (11) :1171-1183

[7] CARBOHYDRATE-PROTEIN INTERACTIONS - BASIS OF GLYCOBIOLOGY [J].

LEE, YC ;

LEE, RT .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (08) :321-327

[8] Structure-reactivity relationships for the inhibition mechanism at the second alkyl-chain-binding site of cholesterol esterase and lipase [J].

Lin, GL ;

Shieh, CT ;

Ho, HC ;

Chouhwang, JY ;

Lin, WY ;

Lu, CP .

BIOCHEMISTRY, 1999, 38 (31) :9971-9981

[9] Chemoenzymatically synthesized glycoconjugate polymers [J].

Miura, Y ;

Ikeda, T ;

Kobayashi, K .

BIOMACROMOLECULES, 2003, 4 (02) :410-415

[10]

SERGIO R, 1988, J AM CHEM SOC, V110, P584

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