GLYCOSYLIMIDATES .53. DIRECT SYNTHESIS OF NUCLEOSIDE MONOPHOSPHATE SUGARS SYNTHESIS OF GMP-FUCOSE

被引：11

作者：

SCHMIDT, RR

BRAUN, H

JUNG, KH

机构：

[1] Fakultät Chemie, Universität Konstanz, D-7750 Konstanz

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 12期

关键词：

D O I：

10.1016/S0040-4039(00)91680-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

O-(2,3,4-Tri-O-acetyl-alpha-L-fucopyranosyl)-trichloroacetimidate 1 furnished with acetyl protected UMP, AMP, and GMP derivatives 3a-c directly alpha,beta anomeric mixtures of the corresponding nucleoside monophosphate fucopyranoses. Immediate deacetylation led to the unprotected target molecules 4a-alpha/beta-4c-alpha/beta. The anomeric mixtures of 4b-alpha/beta and 4c-alpha/beta were separable by preparative HPLC; thus, the desired GMP-beta-fucose (4c-beta) was obtained in pure form.

引用

收藏

页码：1585 / 1588

页数：4

相关论文

共 19 条

[1] GLYCOSPHINGOLIPIDS AND ANTITUMOR IMMUNITY [J].

DYATLOVITSKAYA, EV ;

BERGELSON, LD .

BIOCHIMICA ET BIOPHYSICA ACTA, 1987, 907 (02) :125-143

[2] 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

[3]

HAKOMORI S, 1985, CANCER RES, V45, P2405

[4] GLYCOSPHINGOLIPIDS IN CELLULAR INTERACTION, DIFFERENTIATION, AND ONCOGENESIS [J].

HAKOMORI, SI .

ANNUAL REVIEW OF BIOCHEMISTRY, 1981, 50 :733-764

[5] TUMOR-ASSOCIATED GLYCOLIPID ANTIGENS, THEIR METABOLISM AND ORGANIZATION [J].

HAKOMORI, SI .

CHEMISTRY AND PHYSICS OF LIPIDS, 1986, 42 (1-3) :209-233

[6] BIOSYNTHESIS OF DIGALACTOSYLDIACYLGLYCEROL IN PLASTIDS FROM 16-3 AND 18-3 PLANTS [J].

HEEMSKERK, JWM ;

STORZ, T ;

SCHMIDT, RR ;

HEINZ, E .

PLANT PHYSIOLOGY, 1990, 93 (04) :1286-1294

[7] ACETYL DERIVATIVES OF NUCLEOSIDE 5'-TRIPHOSPHATES .1. [J].

MARIAN, M .

MICROCHEMICAL JOURNAL, 1984, 29 (02) :219-227

[8]

QIU D, UNPUB LIEBIGS ANN CH

[9] STUDIES ON POLYNUCLEOTIDES .16. SPECIFIC SYNTHESIS OF C3'-C5' INTERRIBONUCLEOTIDIC LINKAGE - EXAMINATION OF ROUTES INVOLVING PROTECTED RIBONUCLEOSIDES AND RIBONUCLEOSIDE-3' PHOSPHATES - SYNTHESES OF URIDYLYL-(3'-]5')-ADENOSINE, URIDYLYL-(3'-]5')-CYTIDINE, ADENYL-(3'-]5')-ADENOSINE AND RELATED COMPOUNDS [J].

RAMMLER, DH ;

KHORANA, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (16) :3112-&

[10]

Schmidt R. R., 1986, ANGEW CHEM, V98, P213