STEREOSELECTIVE SYNTHESES OF RETRO-ISOMERS OF N-GLUCOASPARAGINE

被引:46
作者
FREY, O [1 ]
HOFFMANN, M [1 ]
KESSLER, H [1 ]
机构
[1] TECH UNIV MUNICH,INST ORGAN CHEM & BIOCHEM,D-85747 GARCHING,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 18期
关键词
C-GLYCOSIDES; GLYCOSYLATED AMINO ACIDS; HEPTONAMIDES;
D O I
10.1002/anie.199520261
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new type of linkage between the anomeric center of a pyranose and an amino acid is represented by the C‐glycosidic amide bond (shown on the right). It was formed by coupling heptonic acids with a β‐aminoalanine derivative. Both the α and the β anomers were prepared selectively. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:2026 / 2028
页数:3
相关论文
共 23 条
[1]   N-SUBSTITUTED (BETA-D-GALACTOPYRANOSYLMETHYL)AMINES, AND C-BETA-D-GALACTOPYRANOSYLFORMAMIDES, AND RELATED-COMPOUNDS [J].
BEMILLER, JN ;
YADAV, MP ;
KALABOKIS, VN ;
MYERS, RW .
CARBOHYDRATE RESEARCH, 1990, 200 :111-126
[2]   N-SUBSTITUTED (BETA-D-GALACTOPYRANOSYLMETHYL) AMINES AS REVERSIBLE INHIBITORS OF BETA-D-GALACTOSIDASE [J].
BEMILLER, JN ;
GILSON, RJ ;
MYERS, RW ;
SANTORO, MM ;
YADAV, MP .
CARBOHYDRATE RESEARCH, 1993, 250 (01) :93-100
[3]   SYNTHESIS OF CARBON-LINKED GLYCOPEPTIDES AS STABLE GLYCOPEPTIDE MODELS [J].
BERTOZZI, CR ;
HOEPRICH, PD ;
BEDNARSKI, MD .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) :6092-6094
[4]   COMPARATIVE MOLECULAR-FIELD ANALYSIS USING GRID FORCE-FIELD AND GOLPE VARIABLE SELECTION METHODS IN A STUDY OF INHIBITORS OF GLYCOGEN-PHOSPHORYLASE-B [J].
CRUCIANI, G ;
WATSON, KA .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (16) :2589-2601
[5]   PEPTIDE TO GLYCOPEPTIDE - GLYCOSYLATED OLIGOPEPTIDE RENIN INHIBITORS WITH ATTENUATED INVIVO CLEARANCE PROPERTIES [J].
FISHER, JF ;
HARRISON, AW ;
BUNDY, GL ;
WILKINSON, KF ;
RUSH, BD ;
RUWART, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (10) :3140-3143
[6]   PREPARATION AND TRANSMETALATION OF A TRIPHENYLSTANNYL BETA-D-GLUCOPYRANOSIDE - A HIGHLY STEREOSELECTIVE ROUTE TO BETA-D-C-GLYCOSIDES VIA GLYCOSYL DIANIONS [J].
FREY, O ;
HOFFMANN, M ;
WITTMANN, V ;
KESSLER, H ;
UHLMANN, P ;
VASELLA, A .
HELVETICA CHIMICA ACTA, 1994, 77 (07) :2060-2069
[7]   DIASTEREOTOPIC SUBSTRATES OF BETA-D-GALACTOSIDASE FROM ESCHERICHIA-COLI AS PROBES FOR A CATALYTICALLY ACTIVE, PROTONATING GROUP [J].
FRITZ, H ;
LEHMANN, J ;
SCHLESSELMANN, P .
CARBOHYDRATE RESEARCH, 1983, 113 (01) :71-92
[8]   POLYSACCHARIDE ANALOGUES .1. SYNTHESES OF 7-AMINO-2,6-ANHYDRO-7-DEOXY-D-GLYCERO-L-MANNO-HEPTONIC ACID AND 7-AMINO-2,6-ANHYDRO-7-DEOXY-D-GLYCERO-D-GULO-HEPTONIC ACID [J].
FUCHS, EF ;
LEHMANN, J .
CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (07) :2254-2260
[9]   STUDIES ON MUCOPROTEINS .4. LINKAGE OF PROSTHETIC GROUP TO PROTEIN CORE IN OVINE SUBMAXILLARY GLAND MUCOPROTEIN [J].
GOTTSCHALK, A ;
MURPHY, WH .
BIOCHIMICA ET BIOPHYSICA ACTA, 1961, 46 (01) :81-+
[10]  
GOTTSCHALK A, 1972, GLYCOPROTEINS THEIR, P361