Bovine heart galectin-1 selects a unique (Syn) conformation of C-lactose, a flexible lactose analogue

被引：87

作者：

Asensio, JL

Espinosa, JF

Dietrich, H

Cañada, FJ

Schmidt, RR

Martín-Lomas, M

André, S

Gabius, HJ

Jiménez-Barbero, J

机构：

[1] CSIC, Inst Quim Organ, Dept Quim Organ Biol, E-28006 Madrid, Spain

[2] Univ Munich, Tierarztl Fak, Inst Physiol Chem, D-80539 Munich, Germany

[3] Univ Konstanz, Inst Organ Chem, D-78464 Constance, Germany

[4] CSIC, Inst Invest Quim, E-41080 Seville, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 39期

关键词：

D O I：

10.1021/ja990601u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The C-glycoside analogue of lactose harbors a pronounced flexibility in water with three conformers in equilibrium. The bound conformation of C-lactose to bovine heart galectin-1 in solution has been determined by NMR spectroscopy. It is demonstrated that the lectin selects the syn conformation of the structural analogue of natural lactose and not the global minimum, anti conformation. The bound conformer resembles those found in the crystal structures of complexes of galectin-1/N-acetyllactosamine-containing oligosaccharides and in solution for an avian galectin. Docking of the analogue within the galectin's binding site furnishes explanations, in structural terms, for the exclusive recognition of the syn conformer.

引用

页码：8995 / 9000

页数：6

共 54 条

[1] Neoglycoproteins with the synthetic complex biantennary nonasaccharide or its alpha 2,3/alpha 2,6-sialylated derivatives: Their preparation, assessment of their ligand properties for purified lectins, for tumor cells in vitro, and in tissue sections, and their biodistribution in tumor-bearing mice
Andre, S
Unverzagt, C
Kojima, S
Dong, X
Fink, C
Kayser, K
Gabius, HJ
[J]. BIOCONJUGATE CHEMISTRY, 1997, 8 (06) : 845 - 855
[2] [Anonymous], 1997, GLYCOSCIENCES STATUS
[3] STUDIES OF THE BOUND CONFORMATIONS OF METHYL ALPHA-LACTOSIDE AND METHYL BETA-ALLOLACTOSIDE TO RICIN-B CHAIN USING TRANSFERRED NOE EXPERIMENTS IN THE LABORATORY AND ROTATING FRAMES, ASSISTED BY MOLECULAR MECHANICS AND DYNAMICS CALCULATIONS
ASENSIO, JL
CANADA, FJ
JIMENEZBARBERO, J
[J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1995, 233 (02): : 618 - 630
[4] THE USE OF THE AMBER FORCE-FIELD IN CONFORMATIONAL-ANALYSIS OF CARBOHYDRATE MOLECULES - DETERMINATION OF THE SOLUTION CONFORMATION OF METHYL ALPHA-LACTOSIDE BY NMR-SPECTROSCOPY, ASSISTED BY MOLECULAR MECHANICS AND DYNAMICS CALCULATIONS
ASENSIO, JL
JIMENEZBARBERO, J
[J]. BIOPOLYMERS, 1995, 35 (01) : 55 - 73
[5] NMR investigations of protein-carbohydrate interactions:: refined three-dimensional structure of the complex between hevein and methyl β-chitobioside
Asensio, JL
Cañada, FJ
Bruix, M
González, C
Khiar, N
Rodríguez-Romero, A
Jiménez-Barbero, J
[J]. GLYCOBIOLOGY, 1998, 8 (06) : 569 - 577
[6] CROSS-LINKING OF MAMMALIAN LECTIN (GALECTIN-1) BY COMPLEX BIANTENNARY SACCHARIDES
BOURNE, Y
BOLGIANO, B
LIAO, DL
STRECKER, G
CANTAU, P
HERZBERG, O
FEIZI, T
CAMBILLAU, C
[J]. NATURE STRUCTURAL BIOLOGY, 1994, 1 (12): : 863 - 870
[7] Bundle D. R, 1992, CURR OPIN STRUC BIOL, V2, P666, DOI DOI 10.1016/0959-440X(92)90199-H
[8] CONFORMATIONAL MOBILITY OF OLIGOSACCHARIDES - EXPERIMENTAL-EVIDENCE FOR THE EXISTENCE OF AN ANTI CONFORMER OF THE GA1-BETA-1-3GLC-BETA-1-OME DISACCHARIDE
DABROWSKI, J
KOZAR, T
GROSSKURTH, H
NIFANTEV, NE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (20) : 5534 - 5539
[9] Conformational differences of O- and C-glycosides in the protein-bound state: Different conformations of C-lactose and its O-analogue are recognized by ricin B, a galactose-binding protein
Espinosa, JF
Canada, FJ
Asensio, JL
Dietrich, H
MartinLomas, M
Schmidt, RR
JimenezBarbero, J
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (03): : 303 - 306
[10] Conformational flexibility of C-glycosides: Experimental evidence of the existence of a Gauche-Gauche conformation around the glycosidic linkage for a lactose analogue
Espinosa, JF
Dietrich, HJ
MartinLomas, M
Schmidt, RR
JimenezBarbero, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (09) : 1467 - 1470

← 1 2 3 4 5 6 →