COMPONENTS OF OLIGOSACCHARIDES .96. SYNTHESIS OF PARTIAL STRUCTURES OF N-GLYCOPROTEINS OF THE COMPLEX TYPE

被引:66
作者
PAULSEN, H
HELPAP, B
机构
关键词
D O I
10.1016/0008-6215(92)84169-S
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
Comparable syntheses of beta-D-GlcpNAc-(1 --> 2)-[beta-D-GlcpNac--(1 --> 6)]-alpha-D-Manp-(1 --> 6)-beta-D-ManpO(CH2)8CO2Me and beta-D-GlcpNAc-(1 --> 2)-alpha-D-Manp-(1 --> 3)-beta-D-ManpO(CH2)8CO2Me with the glycosyl halide and imidate methods were investigated. 3,4,6-Tri-O-acetyl-2-deoxy-(2,2,2-trichloroethoxycarbonylamino)-alpha-D-glucopyranosyl bromide or trichloroacetimidate are suitable glycosyl donors for beta-D-glycoside coupling with secondary hydroxyl groups.
引用
收藏
页码:289 / 313
页数:25
相关论文
共 27 条
[1]  
BOOMER WA, 1958, J AM CHEM SOC, V80, P3372
[2]  
BROCKHAUSEN I, 1989, J BIOL CHEM, V264, P11211
[3]   PREPARATION AND SYNTHETIC UTILITY OF TERT-BUTYLDIPHENYLSILYL ETHERS [J].
HANESSIAN, S ;
LAVALLEE, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1975, 53 (19) :2975-2977
[4]   THE TRISACCHARIDE BETA-D-GLCPNAC-(1-]2)-ALPHA-D-MANP-(1-]6)-BETA-D-MANP, AS ITS 8-METHOXYCARBONYLOCTYL GLYCOSIDE, IS AN ACCEPTOR SELECTIVE FOR N-ACETYLGLUCOSAMINYLTRANSFERASE-V [J].
HINDSGAUL, O ;
TAHIR, SH ;
SRIVASTAVA, OP ;
PIERCE, M .
CARBOHYDRATE RESEARCH, 1988, 173 (02) :263-272
[5]   TOTAL SYNTHESIS OF ESCHERICHIA-COLI LIPID-A, THE ENDOTOXICALLY ACTIVE PRINCIPLE OF CELL-SURFACE LIPOPOLYSACCHARIDE [J].
IMOTO, M ;
YOSHIMURA, H ;
SHIMAMOTO, T ;
SAKAGUCHI, N ;
KUSUMOTO, S ;
SHIBA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2205-2214
[6]  
Lemieux R. U., 1976, ACS SYM SER, V39, P90, DOI DOI 10.1021/BK-1977-0039.CH006
[7]   PROPERTIES OF A SYNTHETIC ANTIGEN RELATED TO HUMAN BLOOD-GROUP LEWIS-A [J].
LEMIEUX, RU ;
BUNDLE, DR ;
BAKER, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (14) :4076-4083
[8]   IODINE AS A REAGENT FOR THE READY HYDROLYSIS OF PROP-1-ENYL GLYCOSIDES, OR THEIR CONVERSION INTO OXAZOLINES [J].
NASHED, MA ;
ANDERSON, L .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (21) :1274-1276
[9]  
NISHIKAWA Y, 1988, J BIOL CHEM, V263, P8270
[10]   SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .29. SYNTHESIS OF A BRANCHED MANNOHEXAOSIDE, A PART STRUCTURE OF A HIGH-MANNOSE-TYPE GLYCAN OF A GLYCOPROTEIN [J].
OGAWA, T ;
NUKADA, T .
CARBOHYDRATE RESEARCH, 1985, 136 (FEB) :135-152