2-BROMOETHYL GLYCOSIDES .6. SYNTHESIS FROM PULLULAN OF SPACER-ARM, LIPID, AND ETHYL GLYCOSIDES OF A TETRASACCHARIDE [ALPHA-D-GLC-(1-]6)-ALPHA-D-GLC-(1-]4)-ALPHA-D-GLC-(1-]4)-D-GLC] FOUND IN HUMAN-URINE - PREPARATION OF NEOGLYCOPROTEINS

被引：10
作者：
DAHMEN, J
FREJD, T
MAGNUSSON, G
NOORI, G
CARLSTROM, AS
机构：
来源：
CARBOHYDRATE RESEARCH | 1984年 / 127卷 / 01期
关键词：
D O I：
10.1016/0008-6215(84)85103-4
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：
Enzymic hydrolysis of pullulan, followed by acetylation and chromatography, gave acetylated .alpha.-D-Glcp-(1 .fwdarw. 6)-.alpha.-D-Glcp-(1 .fwdarw. 4)-.alpha.-D-Glcp-(1 .fwdarw. 4)-D-Glcp which, with 2-bromoethanol and boron trifluoride etherate in dichloromethane, gave the 2-bromoethyl glycoside. The reactions of the glycoside with methyl 3-mercaptopropionate, methyl 11-mercaptoundecanoate and octadecanethiol as well as its hydrogenolysis to give an ethyl glycoside are described. The mercaptopropionate-derived, spacer-arm glycoside was coupled to bovine serum albumin and keyhole limpet hemocyanin.
引用
收藏
页码：27 / 33
页数：7
相关论文
共 50 条
[21]   SYNTHETIC ANTIGENS - SYNTHESIS OF 4-AMINOPHENYL O-ALPHA-D-MANNOPYRANOSYL-(1-]2)-O-ALPHA-D-MANNOPYRANOSYL-(1-]6)-O-ALPHA-D-MANNOPYRANOSIDE AND A RELATED DISACCHARIDE AND A TRISACCHARIDE [J].
KHAN, SH ;
PISKORZ, CF ;
MATTA, KL .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (07) :1025-1035
[22]   SYNTHESIS OF O-ALPHA-L-FUCOPYRANOSYL-(1-]6)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-D-GLUCOPYRANOSE "(6'-O-ALPHA-L-FUCOPYRANOSYLLACTOSE) [J].
BAER, HH ;
ABBAS, SA .
CARBOHYDRATE RESEARCH, 1980, 83 (01) :146-151
[23]   GLUCAN SYNTHESIS .7. TOTAL SYNTHESIS OF CYCLOMALTOOCTAOSE AND AN ISOMER OF CYCLOMALTOHEXAOSE, CYCLO(-]6)-[ALPHA-D-GLCP-(1-]4)]5-ALPHA-D-GLCP-(1-) [J].
TAKAHASHI, Y ;
OGAWA, T .
CARBOHYDRATE RESEARCH, 1987, 169 :127-149
[24]   SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .31. SYNTHESIS OF ALPHA-NEU5ACP-(2-]3)-D-GAL AND ALPHA-NEU5ACP-(2-]3)-BETA-D-GALP-(1-]4)-D-GLC [J].
OGAWA, T ;
SUGIMOTO, M .
CARBOHYDRATE RESEARCH, 1985, 135 (02) :C5-C9
[25]   SYNTHESIS OF OLIGOSACCHARINS - A CHEMICAL SYNTHESIS OF PROPYL O-BETA-D-GALACTOPYRANOSYL-(1-]2)-O-ALPHA-D-XYLOPYRANOSYL-(1-]6)-O-BETA-D-GLUCOPYRANOSYL-(1-]4)-BETA-D-GLUCOPYRANOSIDE [J].
WOTOVIC, A ;
JACQUINET, JC ;
SINAY, P .
CARBOHYDRATE RESEARCH, 1990, 205 :235-245
[26]   CONTROL OF GLYCOPROTEIN-SYNTHESIS - CHARACTERIZATION OF (1-]4)-N-ACETYL-BETA-D-GLUCOSAMINYLTRANSFERASES ACTING ON THE ALPHA-D-(1-]3)-LINKED AND ALPHA-D-(1-]6)-LINKED ARMS OF N-LINKED OLIGOSACCHARIDES [J].
BROCKHAUSEN, I ;
MOLLER, G ;
YANG, JM ;
KHAN, SH ;
MATTA, KL ;
PAULSEN, H ;
GREY, AA ;
SHAH, RN ;
SCHACHTER, H .
CARBOHYDRATE RESEARCH, 1992, 236 :281-299
[27]   OLIGOSACCHARIDES RELATED TO TUMOR-ASSOCIATE ANTIGENS .3. SYNTHESIS OF THE PROPYL GLYCOSIDES OF THE TRISACCHARIDE BETA-D-GALP-(1-]3)-BETA-D-GALPNAC-(1-]3)-ALPHA-D-GALP AND OF THE TETRASACCHARIDE ALPHA-L-FUCP-(1-]2)-BETA-D-GALP-(1-]3)-BETA-D-GALPNAC-(1-]3)-ALPHA-D-GALP, COMPONENTS OF A TUMOR-ANTIGEN RECOGNIZED BY THE ANTIBODY MBR1 [J].
LAY, L ;
PANZA, L ;
RUSSO, G ;
COLOMBO, D ;
RONCHETTI, F ;
ADOBATI, E ;
CANEVARI, S .
HELVETICA CHIMICA ACTA, 1995, 78 (03) :533-538
[28]   SYNTHESIS OF BLOOD-GROUP SUBSTANCES .6. SYNTHESIS OF O-ALPHA-L-FUCOPYRANOSYL-(1-]2)-O-BETA-D-GALACTOPYRANOSYL-(1-]4)-O-[ALPHA-L-FUCOPYRANOSYL-(1-]3)]-2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE, POSTULATED LEWIS-D ANTIGENIC DETERMINANT [J].
JACQUINET, JC ;
SINAY, P .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :720-724
[29]   CHEMICAL SYNTHESIS OF POLYSACCHARIDES .9. CHEMICAL SYNTHESIS OF 4-DEOXY-(1-]6)-ALPHA-D-XYLO-HEXOPYRANAN AND 3,4-DIDEOXY-(1-]6)-ALPHA-D-ERYTHRO-HEXOPYRANAN [J].
OKADA, M ;
BANNO, A ;
SUMITOMO, H .
CARBOHYDRATE RESEARCH, 1992, 226 (02) :345-352
[30]   SYNTHESIS OF POLYSACCHARIDES - GLUCORHAMNAN -]6-D-GLCP 1-]-BETA-4-L-RHAP1-]ALPHA [J].
KOCHETKOV, NK ;
KLIMOV, EM .
TETRAHEDRON LETTERS, 1981, 22 (04) :337-340
12345