Rapid conversion of unprotected galactose analogs to their UDP-derivatives for use in the chemo-enzymatic synthesis of unnatural oligosaccharides

被引:32
作者
Uchiyama, T [1 ]
Hindsgaul, O [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1080/07328309808001892
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 rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).
引用
收藏
页码:1181 / 1190
页数:10
相关论文
共 13 条
[1]   RAPID CHEMICAL SYNTHESIS OF SUGAR NUCLEOTIDES IN A FORM SUITABLE FOR ENZYMATIC OLIGOSACCHARIDE SYNTHESIS [J].
ARLT, M ;
HINDSGAUL, O .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01) :14-15
[2]   STRUCTURE-FUNCTION-RELATIONSHIPS IN LACTOSE SYNTHASE - STRUCTURAL REQUIREMENTS OF THE URIDINE 5'-DIPHOSPHATE GALACTOSE BINDING-SITE [J].
BERLINER, LJ ;
ROBINSON, RD .
BIOCHEMISTRY, 1982, 21 (25) :6340-6343
[3]   SILYL PROTECTION IN THE SOLID-PHASE SYNTHESIS OF N-LINKED NEOGLYCOPEPTIDES - ONE-STEP DEPROTECTION OF FULLY PROTECTED NEOGLYCOPEPTIDES [J].
CHRISTIANSENBRAMS, I ;
MELDAL, M ;
BOCK, K .
TETRAHEDRON LETTERS, 1993, 34 (20) :3315-3318
[4]   CHEMICAL SYNTHESIS OF GDP-FUCOSE ANALOGS AND THEIR UTILIZATION BY THE LEWIS ALPHA(1-]4) FUCOSYL-TRANSFERASE [J].
GOKHALE, UB ;
HINDSGAUL, O ;
PALCIC, MM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (07) :1063-1071
[5]  
HINDSGAUL O, 1991, ACS SYM SER, V466, P38
[6]   ENZYME-CATALYZED OLIGOSACCHARIDE SYNTHESIS [J].
ICHIKAWA, Y ;
LOOK, GC ;
WONG, CH .
ANALYTICAL BIOCHEMISTRY, 1992, 202 (02) :215-238
[7]   SYNTHESIS OF UDP-6-DEOXY-D-GALACTOSES AND UDP-6-FLUORO-D-GALACTOSES AND THEIR ENZYMATIC GLYCOSYL TRANSFER TO MONOANTENNARY AND BIANTENNARY CARBOHYDRATE CHAINS [J].
KODAMA, H ;
KAJIHARA, Y ;
ENDO, T ;
HASHIMOTO, H .
TETRAHEDRON LETTERS, 1993, 34 (40) :6419-6422
[8]   Glycosyltransferases in the synthesis of oligosaccharide analogs [J].
Palcic, MM ;
Hindsgaul, O .
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 1996, 8 (39) :37-49
[9]  
SALAM MA, 1982, CARBOHYD RES, V101, P339, DOI 10.1016/S0008-6215(00)81017-4
[10]  
SCHACHTER H, 1994, MOL GLYCOBIOLOGY, P88