Stereoselective synthesis of NEO-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions

被引:14
作者
Arya, P
Dion, S
Shimizu, GKH
机构
[1] Steacie Inst. for Molecular Sciences, National Research Council of Canada, Ottawa
关键词
D O I
10.1016/S0960-894X(97)00255-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Neo-C-glycopeptides (1-4) have been synthesized as building blocks to obtain higher neo-C-glycopeptides as probes for studying carbohydrate-protein interactions. A convergent approach for the synthesis of 4 has been developed, in which two galactose units are attached to a glycine derivative in a stepwise procedure (reductive amination followed by amide coupling) and finally coupling to the protected dipeptide having a free amino group on the side chain. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:1537 / 1542
页数:6
相关论文
共 47 条
[1]   REDUCTIVE AMINATION OF ALDEHYDES AND KETONES BY USING SODIUM TRIACETOXYBOROHYDRIDE [J].
ABDELMAGID, AF ;
MARYANOFF, CA ;
CARSON, KG .
TETRAHEDRON LETTERS, 1990, 31 (39) :5595-5598
[2]   KMNO4 REVISITED - OXIDATION OF ALDEHYDES TO CARBOXYLIC-ACIDS IN THE TERT-BUTYL ALCOHOL AQUEOUS NAH2PO4 SYSTEM [J].
ABIKO, A ;
ROBERTS, JC ;
TAKEMASA, T ;
MASAMUNE, S .
TETRAHEDRON LETTERS, 1986, 27 (38) :4537-4540
[3]   GLOBULAR CARBOHYDRATE MACROMOLECULE SUGAR BALLS .1. SYNTHESIS OF NOVEL SUGAR-PERSUBSTITUTED POLY(AMIDO AMINE) DENDRIMERS [J].
AOI, K ;
ITOH, K ;
OKADA, M .
MACROMOLECULES, 1995, 28 (15) :5391-5393
[4]  
ARYA P, UNPUB
[5]  
ARYA P, 1997, IN PRESS ANGEW CHEM
[6]   Synthetic carbohydrate dendrimers .1. A convergent synthesis of carbohydrate-containing dendrimers [J].
Ashton, PR ;
Boyd, SE ;
Brown, CL ;
Jayaraman, N ;
Nepogodiev, SA ;
Stoddart, JF .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (09) :1115-1128
[7]   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
[8]   GALACTOSE AT THE NONREDUCING TERMINUS OF O-LINKED OLIGOSACCHARIDES OF MOUSE EGG ZONA PELLUCIDA GLYCOPROTEIN ZP3 IS ESSENTIAL FOR THE GLYCOPROTEINS SPERM RECEPTOR ACTIVITY [J].
BLEIL, JD ;
WASSARMAN, PM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (18) :6778-6782
[9]  
Bruning J, 1996, TETRAHEDRON LETT, V37, P2907
[10]  
CERVIGNI SE, 1996, INT ED ENGL, V35, P1230