SYNTHESIS OF O-BETA-D-GALACTOPYRANOSYL-(1-3)-O-BETA-D-GALACTOPYRANOSYL-(1-4)-O-BETA-D-XYLOPYRANOSYL-(1-3)-L-SERINE (GAL-GAL-XYL-SER)

被引：23
作者：
EKBORG, G
CURENTON, T
KRISHNA, NR
RODEN, L
机构：
[1] UNIV ALABAMA,MED GENET LAB,BIRMINGHAM,AL 35294
[2] UNIV ALABAMA,CTR NMR CORE FACIL COMPREHENS CANC,BIRMINGHAM,AL 35294
[3] UNIV ALABAMA,DEPT BIOCHEM,BIRMINGHAM,AL 35294
[4] UNIV ALABAMA,DEPT MED,BIRMINGHAM,AL 35294
来源：
JOURNAL OF CARBOHYDRATE CHEMISTRY | 1990年 / 9卷 / 01期
基金：
美国国家卫生研究院; 美国国家科学基金会;
关键词：
D O I：
10.1080/07328309008545795
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：
O-β-D-Galactopyranoayl-(1—>3)-O-β-D-galactopyranosyl-(1—>4)-O-β-D-xylopyranosyl-(1—>3)-L-serine (Gal-Gal-Xyl-Ser) was prepared by a procedure involving the synthesis of a benzoylated galactobiosyl bromide and a xylosylserine derivative with an unsubstituted hydroxyl group at C-4 (3-0-(2, 3-di-O-benzoyl-β-D-xylopyranosyl)-N-carbobenzoxy-L-serine benzyl ester), followed by condensation and deblocking. The structure of the product was confirmed by 1H-and 13C-NMR spectroscopy. Upon incubation with an extract of embryonic chick cartilage, the synthetic Gal-Gal-Xyl-Ser served as an acceptor for enzymatic glucuronosyl transfer from UDP-D-glucuronic acid. © 1990, Taylor & Francis Group, LLC. All rights reserved.
引用
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页码：15 / 37
页数：23
相关论文
共 38 条
[1]   REGIOSELECTIVE MONO-O-ALKYLATION OF DISACCHARIDE GLYCOSIDES THROUGH THEIR DIBUTYLSTANNYLENE COMPLEXES [J].
ALAIS, J ;
MARANDUBA, A ;
VEYRIERES, A .
TETRAHEDRON LETTERS, 1983, 24 (23) :2383-2386
[2]  
ANWER MK, 1980, SYNTHESIS-STUTTGART, P929
[3]   NEW SYNTHESIS OF 3-O-BETA-D-GALACTOPYRANOSYL-D-GALACTOSE [J].
BENZINGNGUYEN, L ;
RODEN, L .
CARBOHYDRATE RESEARCH, 1977, 53 (01) :123-128
[4]  
Brendel K., 1966, CARBOHYD RES, V2, P42
[5]   A MILD PROCEDURE FOR THE REGIOSPECIFIC BENZYLATION AND ALLYLATION OF POLYHYDROXY-COMPOUNDS VIA THEIR STANNYLENE DERIVATIVES IN NON-POLAR SOLVENTS [J].
DAVID, S ;
THIEFFRY, A ;
VEYRIERES, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06) :1796-1801
[6]   BROMINOLYSIS REACTION OF STANNYLENE DERIVATIVES - REGIOSPECIFIC SYNTHESIS OF CARBOHYDRATE-DERIVED HYDROXY-KETONES [J].
DAVID, S ;
THIEFFRY, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (06) :1568-1573
[7]  
EFRON ML, 1968, CHROMATOGR ELECTROPH, V2, P171
[8]   SYNTHESIS OF 3-O-BETA-D-XYLOPYRANOSYL-L-SERINE (XYLOSYLSERINE) AND O-BETA-D-GALACTOPYRANOSYL-(1-4)-O-BETA-D-XYLOPYRANOSYL-L-SERINE (GALACTOSYLXYLOSYLSERINE) AND USE OF THE SYNTHETIC PRODUCTS FOR DETECTION OF GALACTOSYLTRANSFERASE-I ACTIVITY IN RAT-LIVER [J].
EKBORG, G ;
KLINGER, M ;
RODEN, L ;
JENSEN, JW ;
SCHUTZBACH, JS ;
HUANG, DH ;
KRISHNA, NR ;
ANANTHARAMAIAH, GM .
GLYCOCONJUGATE JOURNAL, 1987, 4 (03) :255-266
[9]   REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].
ELAMIN, B ;
ANANTHARAMAIAH, GM ;
ROYER, GP ;
MEANS, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444
[10]   SYNTHESIS OF O-BETA-D-GALACTOPYRANOSYL-(1-]4)-O-BETA-D-XYLOPYRANOSYL-L-SERINE [J].
ERBING, B ;
LINDBERG, B ;
NORBERG, T .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1978, 32 (04) :308-310
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