Solution phase synthesis of (1->5)-amide linked sugar amino acid dimers derived from sialic acids

被引:41
作者
Gervay, J
Flaherty, TM
Nguyen, C
机构
[1] Department of Chemistry, University of Arizona, Tucson
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(97)00138-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carboxy-protected amino derivatives and amino-protected carboxy derivatives of three different C-2 analogs as well as a 2,3-dehydro NeuAc were prepared. These monomers were coupled in solution using BOP activation of the carboxy terminus to form (1-->5)-amide linked dimers of sialyl amino acid derivatives. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1493 / 1496
页数:4
相关论文
共 25 条
[1]  
APOSTOLOPOULOS CD, 1994, LIEBIGS ANN CHEM, P781
[2]   SYNTHESIS OF ALPHA,BETA-UNSATURATED ANALOGS OF KDO AND N-ACETYLNEURAMINIC ACID BY TRIMETHYLSILYL TRIFLATE-CATALYZED ELIMINATION-REACTIONS [J].
CLAESSON, A ;
LUTHMAN, K .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (10) :719-720
[3]   SYNTHESIS OF TRANSITION-STATE ANALOGS AS POTENTIAL INHIBITORS OF SIALIDASE FROM INFLUENZA-VIRUS [J].
DRIGUEZ, PA ;
BARRERE, B ;
QUASH, G ;
DOUTHEAU, A .
CARBOHYDRATE RESEARCH, 1994, 262 (02) :297-310
[4]   A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS [J].
FLYNN, DL ;
ZELLE, RE ;
GRIECO, PA .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) :2424-2426
[5]   REMOVAL OF FORMYL, ACETYL, AND BENZOYL GROUPS FROM AMIDES WITH CONVERSION INTO THE CORRESPONDING TERT-BUTYL CARBAMATES [J].
GREHN, L ;
GUNNARSSON, K ;
RAGNARSSON, U .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (19) :1317-1318
[6]  
HANESSIA.S, 1967, TETRAHEDRON LETT, P1549
[7]   SYNTHESIS OF COMPLEX NUCLEOSIDE ANTIBIOTICS [J].
KNAPP, S .
CHEMICAL REVIEWS, 1995, 95 (06) :1859-1876
[8]   Glycosamino acids: New building blocks for combinatorial synthesis [J].
McDevitt, JP ;
Lansbury, PT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (16) :3818-3828
[9]   CONFORMATIONAL DIFFERENCES BETWEEN LINEAR ALPHA(2-]8)-LINKED HOMOSIALOOLIGOSACCHARIDES AND THE EPITOPE OF THE GROUP-B MENINGOCOCCAL POLYSACCHARIDE [J].
MICHON, F ;
BRISSON, JR ;
JENNINGS, HJ .
BIOCHEMISTRY, 1987, 26 (25) :8399-8405
[10]  
MULLER C, 1995, J CHEM SOC CHEM COMM, P2425