A facile preparation of the methyl 2-thioglycoside of N-glycolylneuraminic acid, an efficient donor of NeuGc

被引:33
作者
Sugata, T [1 ]
Higuchi, R [1 ]
机构
[1] KYUSHU UNIV,FAC PHARMACEUT SCI,HIGASHI KU,FUKUOKA 81282,JAPAN
关键词
D O I
10.1016/0040-4039(96)00383-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The methyl 2-thioglycoside of N-glycolylneuraminic acid (SMe-NeuGc, 1), which is an efficient donor of NeuGc in the preparation of sialosyl glycoconjugates, was synthesized from N-acetylneuraminic acid (NeuAc) in 6 steps in good yield. 1 could be glycosylated with two lactose accepters to give sialosyl oligosaccharides 8, 9 and 10 in high yields. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:2613 / 2614
页数:2
相关论文
共 16 条
[1]  
BREMER EG, 1986, J BIOL CHEM, V261, P2434
[2]   FLUOROMETRIC HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF N-ACETYLNEURAMINIC AND N-GLYCOLYLNEURAMINIC ACIDS AND ITS APPLICATION TO THEIR MICRODETERMINATION IN HUMAN AND ANIMAL SERA, GLYCOPROTEINS, AND GLYCOLIPIDS [J].
HARA, S ;
TAKEMORI, Y ;
YAMAGUCHI, M ;
NAKAMURA, M ;
OHKURA, Y .
ANALYTICAL BIOCHEMISTRY, 1987, 164 (01) :138-145
[3]   SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .19. A FACILE, LARGE-SCALE PREPARATION OF THE METHYL 2-THIOGLYCOSIDE OF N-ACETYLNEURAMINIC ACID, AND ITS USEFULNESS FOR THE ALPHA-STEREOSELECTIVE SYNTHESIS OF SIALOGLYCOSIDES [J].
HASEGAWA, A ;
OHKI, H ;
NAGAHAMA, T ;
ISHIDA, H ;
KISO, M .
CARBOHYDRATE RESEARCH, 1991, 212 :277-281
[4]   SYNTHETIC STUDIES ON SIALOGLYCO-CONJUGATES .67. SYNTHESIS OF A SIALYL-LEWIS-X GANGLIOSIDE ANALOG CONTAINING N-GLYCOLYL IN-PLACE OF THE N-ACETYL GROUP IN THE N-ACETYLNEURAMINIC ACID RESIDUE [J].
HASEGAWA, A ;
UCHIMURA, A ;
ISHIDA, H ;
KISO, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (06) :1091-1094
[5]  
HIGASHI H, 1985, CANCER RES, V45, P3796
[6]  
HIGUCHI R, 1993, LIEBIGS ANN CHEM, P359
[7]   A SIMPLE METHOD TO DETERMINE THE ANOMERIC CONFIGURATION OF SIALIC-ACID AND ITS DERIVATIVES BY C-13-NMR [J].
HORI, H ;
NAKAJIMA, T ;
NISHIDA, Y ;
OHRUI, H ;
MEGURO, H .
TETRAHEDRON LETTERS, 1988, 29 (48) :6317-6320
[8]   2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES .3. SYNTHESIS, ANOMERIC DEBLOCKING, AND TRANSFORMATION INTO 1,2-TRANS 1-O-ACYL SUGARS [J].
JANSSON, K ;
AHLFORS, S ;
FREJD, T ;
KIHLBERG, J ;
MAGNUSSON, G ;
DAHMEN, J ;
NOORI, G ;
STENVALL, K .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) :5629-5647
[9]  
KAWAI T, 1991, CANCER RES, V51, P1242
[10]   FISH EGG POLYSIALOGLYCOPROTEINS - CIRCULAR-DICHROISM AND PROTON NUCLEAR MAGNETIC-RESONANCE STUDIES OF NOVEL OLIGOSACCHARIDE UNITS CONTAINING ONE SIALIDASE-RESISTANT N-GLYCOLYLNEURAMINIC ACID RESIDUE IN EACH MOLECULE [J].
KITAJIMA, K ;
NOMOTO, H ;
INOUE, Y ;
IWASAKI, M ;
INOUE, S .
BIOCHEMISTRY, 1984, 23 (02) :310-316