Chemo-enzymatic supported synthesis of the 3-sulfated Lewisa pentasaccharide on a multimeric polyethylene glycol

被引：5

作者：

Malleron, Annie ^{[1
]}

Le Narvor, Christine ^{[1
]}

机构：

[1] Univ Paris 11, Equipe Glycochim Mol & Macromol, Lab Chim Organ Multifonctionnelle, CNRS,UMR 8182, F-91405 Orsay, France

来源：

CARBOHYDRATE RESEARCH | 2008年 / 343卷 / 05期

关键词：

chemo-enzymatic synthesis; multimeric support; glycosyltransferase; Selectins; cell adhesion; inflammation;

D O I：

10.1016/j.carres.2008.01.005

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1 -> 3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1 -> 4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：970 / 976

页数：7

共 26 条

[1] Outstanding stability of immobilized recombinant α(1→3/4)-fucosyltransferases exploited in the synthesis of Lewis a and Lewis x trisaccharides [J].

Augé, C ;

Malleron, A ;

Tahrat, H ;

Marc, A ;

Goergen, JL ;

Cerutti, M ;

Steelant, WFA ;

Delannoy, P ;

Lubineau, A .

CHEMICAL COMMUNICATIONS, 2000, (20) :2017-2018

[2] Nuclear magnetic resonance spectroscopy of peracetylated oligosaccharides having 13C-labeled carbonyl groups in lieu of permethylation analysis for establishing linkage substitutions of sugars [J].

Bendiak, B .

CARBOHYDRATE RESEARCH, 1999, 315 (3-4) :206-221

[3]

Benslimane C, 1999, ANIMAL CELL TECHNOLOGY: PRODUCTS FROM CELLS, CELLS AS PRODUCTS, P251

[4] Syntheses of oligomannosides in solution and on a soluble polymer support: a comparison [J].

Blattner, R ;

Furneaux, RH ;

Ludewig, M .

CARBOHYDRATE RESEARCH, 2006, 341 (03) :299-321

[5] Solid-phase enzymatic synthesis of a sialyl Lewis x tetrasaccharide on a sepharose matrix [J].

Blixt, O ;

Norberg, T .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2705-2710

[6] AN IMPROVED PREPARATION OF 3,4-O-ISOPROPYLIDENE DERIVATIVES OF ALPHA-D-GALACTOPYRANOSIDES AND BETA-D-GALACTOPYRANOSIDES [J].

CATELANI, G ;

COLONNA, F ;

MARRA, A .

CARBOHYDRATE RESEARCH, 1988, 182 (02) :297-300

[7] Molecular cloning and characterization of a human β-gal-3′-sulfotransferase that acts on both type 1 and type 2 (Galβ1-3/1-4GlcNAc-R) oligosaccharides [J].

Honke, K ;

Tsuda, M ;

Koyota, S ;

Wada, Y ;

Iida-Tanaka, N ;

Ishizuka, I ;

Nakayama, J ;

Taniguchi, N .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (01) :267-274

[8]

Huang XF, 2001, ADV SYNTH CATAL, V343, P675

[9] EFFICIENT CHEMICAL SYNTHESIS OF GDP-FUCOSE [J].

ICHIKAWA, Y ;

SIM, MM ;

WONG, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2943-2946

[10]

KREPINSKY JJ, 1994, METHOD ENZYMOL, V242, P280

← 1 2 3 →