α-mannosyl clusters scaffolded on azamacrocycles:: Synthesis and inhibitory properties in the adhesion of type 1 fimbriated Escherichia coli to guinea pig erythrocytes

被引:33
作者
König, B
Fricke, T
Wassmann, A
Krallmann-Wenzel, U
Lindhorst, TK
机构
[1] Univ Hamburg, Inst Organ Chem, D-20146 Hamburg, Germany
[2] Forschungszentrum Borstel, D-23845 Borstel, Germany
[3] Gesell Biotechnol Forsch GmbH, D-38124 Braunschweig, Germany
[4] Tech Univ Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany
关键词
macrocycles; glycosides; isothiocyanates; supramolecular chemistry;
D O I
10.1016/S0040-4039(98)00248-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of azamacrocycles, such as la and Ib, with acetyl-protected alpha-D-mannosyl isothiocyanate yields thiourea-bridged tetravalent glycoclusters 3 as novel neoglycoconjugates in one step The deprotected compounds 4 showed significant inhibition of the adhesion of type 1 fimbriated Escherichia coli to Guinea pig erythrocytes. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2307 / 2310
页数:4
相关论文
共 28 条
[11]  
Klemm P., 1994, FIMBRIAE ADHESION GE, P9
[12]  
KROGFELT KA, 1991, REV INFECT DIS, V13, P721
[13]  
LARSKY LA, 1995, ANNU REV BIOCHEM, V64, P113
[14]  
LEE RT, 1987, METHOD ENZYMOL, V138, P424
[15]   CARBOHYDRATE-PROTEIN INTERACTIONS - BASIS OF GLYCOBIOLOGY [J].
LEE, YC ;
LEE, RT .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (08) :321-327
[16]  
LINDHORST TK, 1995, SYNTHESIS-STUTTGART, P1228
[17]   Glycocoating of oligovalent amines: Synthesis of thiourea-bridged cluster glycosides from glycosyl isothiocyanates [J].
Lindhorst, TK ;
Kieburg, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (17) :1953-1956
[18]   Glycodendrimers [J].
Lindhorst, TK .
NACHRICHTEN AUS CHEMIE TECHNIK UND LABORATORIUM, 1996, 44 (11) :1073-&
[19]  
LINDHORST TK, 1996, ANGEW CHEM, V108, P2086
[20]  
MARRA A, 1994, ANGEW CHEM INT EDIT, V33, P2479