Spatial screening of cyclic neoglycopeptides: Identification of polyvalent wheat-germ agglutinin ligands

被引：60

作者：

Wittmann, V ^{[1
]}

Seeberger, S ^{[1
]}

机构：

[1] Goethe Univ Frankfurt, Inst Organ Chem & Chem Biol, D-60439 Frankfurt, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 07期

关键词：

bioorganic chemistry; carbohydrates; glycopeptides; lectins; polyvalency;

D O I：

10.1002/anie.200352055

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Affinities enhanced by up to 619-fold were found for new ligands of the plant lectin wheat-germ agglutinin (compared to the binding of N-acetylglucosamine (GlcNAc)). These polyvalent neoglycopeptides were identified from screening of a spatially diverse library of type 1. Binding affinity is determined not only by the number of GlcNAc residues but also by the ligand architecture.

引用

页码：900 / 903

页数：4

共 38 条

[1]

André S, 2001, CHEMBIOCHEM, V2, P822, DOI 10.1002/1439-7633(20011105)2:11<822::AID-CBIC822>3.0.CO

[2]

2-W

[3] Thermodynamic studies of lectin-carbohydrate interactions by isothermal titration calorimetry [J].

Dam, TK ;

Brewer, CF .

CHEMICAL REVIEWS, 2002, 102 (02) :387-429

[4]

EICHLER J, 1994, PEPTIDE RES, V7, P300

[5] High-affinity pentavalent ligands of Escherichia coli heat-labile enterotoxin by modular structure-based design [J].

Fan, EK ;

Zhang, ZS ;

Minke, WE ;

Hou, Z ;

Verlinde, CLMJ ;

Hol, WGJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (11) :2663-2664

[6] Constrained glycopeptide ligands for MPRs. Limitations of unprotected phosphorylated building blocks [J].

Franzyk, H ;

Christensen, MK ;

Jorgensen, RM ;

Meldal, M ;

Cordes, H ;

Mouritsen, S ;

Bock, K .

BIOORGANIC & MEDICINAL CHEMISTRY, 1997, 5 (01) :21-40

[7] A highly practical synthesis of cyclodextrin-based glycoclusters having enhanced affinity with lectins [J].

Furuike, T ;

Aiba, S ;

Nishimura, SI .

TETRAHEDRON, 2000, 56 (51) :9909-9915

[8] Influencing receptor-ligand binding mechanisms with multivalent ligand architecture [J].

Gestwicki, JE ;

Cairo, CW ;

Strong, LE ;

Oetjen, KA ;

Kiessling, LL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :14922-14933

[9] Glycopeptides as oligosaccharide mimics: High affinity sialopeptide ligands for sialoadhesin from combinatorial libraries [J].

Halkes, KM ;

St Hilaire, PM ;

Crocker, PR ;

Meldal, M .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (01) :18-27

[10]

Haubner R, 1997, ANGEW CHEM INT EDIT, V36, P1375

← 1 2 3 4 →