Efficient synthesis of a sialyl T-antigen-linked glycopeptide by the chemoenzymatic method

被引:12
作者
Ajisaka, K [1 ]
Miyasato, M [1 ]
机构
[1] Meiji Milk Prod Co Ltd, Meiji Inst Hlth Sci, Odawara 2500862, Japan
关键词
peptide synthesis; glycopeptide; mucin-type; beta-galactosidase; sialyltransferase;
D O I
10.1271/bbb.64.1743
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
A sialyl T-antigen-linked tetrapeptide was prepared by the combined method of chemical synthesis and enzymatic synthesis. The GalNAc-linked peptide was first obtained bg using a commercial peptide synthesizer, and then a galactose residue was attached with beta-(1 --> 3)-linkage by transglycosylating with a recombinant beta-galactosidase from Bacillus circulans. The sialic acid residue was then combined by alpha-(2 --> 3)-linkage with sialytransferase from rat liver.
引用
收藏
页码:1743 / 1746
页数:4
相关论文
共 17 条
[1]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[2]  
FLIEGENTHART JFG, 1983, ADV CARBOHYD CHEM, V41, P209
[3]   Purification and properties of recombinant β-galactosidase from Bacillus circulans [J].
Fujimoto, H ;
Miyasato, M ;
Ito, Y ;
Sasaki, T ;
Ajisaka, K .
GLYCOCONJUGATE JOURNAL, 1998, 15 (02) :155-160
[4]   Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant [J].
Gambert, U ;
Thiem, J .
CARBOHYDRATE RESEARCH, 1997, 299 (1-2) :85-89
[5]   DEVELOPMENTS IN THE SYNTHESIS OF GLYCOPEPTIDES CONTAINING GLYCOSYL L-ASPARAGINE, L-SERINE, AND L-THREONINE [J].
GARG, HG ;
VONDEMBRUCH, K ;
KUNZ, H .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 50, 1994, 50 :277-310
[6]   EXPRESSION OF THE MURINE FIBROBLAST GROWTH FACTOR-5 GENE IN THE ADULT CENTRAL-NERVOUS-SYSTEM [J].
HAUB, O ;
DRUCKER, B ;
GOLDFARB, M .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (20) :8022-8026
[7]   SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-3-O-BETA-D-GALACTOPYRANO-SYL-D-GALACTOSE BY THE SEQUENTIAL USE OF BETA-D-GALACTO-SIDASES FROM BOVINE TESTES AND ESCHERICHIA-COLI [J].
HEDBYS, L ;
JOHANSSON, E ;
MOSBACH, K ;
LARSSON, PO ;
GUNNARSSON, A ;
SVENSSON, S .
CARBOHYDRATE RESEARCH, 1989, 186 (02) :217-223
[8]   Cloning and characterization of the gene encoding a novel beta-galactosidase from Bacillus circulans [J].
Ito, Y ;
Sasaki, T .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1997, 61 (08) :1270-1276
[9]   NEW COUPLING REAGENTS IN PEPTIDE CHEMISTRY [J].
KNORR, R ;
TRZECIAK, A ;
BANNWARTH, W ;
GILLESSEN, D .
TETRAHEDRON LETTERS, 1989, 30 (15) :1927-1930
[10]   A MULTIENZYME SYSTEM FOR A ONE-POT SYNTHESIS OF SIALYL T-ANTIGEN [J].
KREN, V ;
THIEM, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08) :893-895