Relationship between structure and three-bond proton-proton coupling constants in glycosaminoglycans

被引：26

作者：

Hricovini, M. ^{[1
]}

Bizik, F.

机构：

[1] Slovak Acad Sci, Inst Chem, Bratislava 84538, Slovakia

[2] Slovak Acad Sci, Inst Virol, Bratislava 84245, Slovakia

来源：

CARBOHYDRATE RESEARCH | 2007年 / 342卷 / 06期

关键词：

glycosaminoglycans; DFT calculations; three-bond coupling constants; conformation; FIBROBLAST-GROWTH-FACTOR; CONFORMATIONAL FLEXIBILITY; IDURONATE RESIDUE; HEPARAN-SULFATE; DENSITY; OLIGOSACCHARIDES; SEQUENCES; DYNAMICS; BINDING; RING;

D O I：

10.1016/j.carres.2007.01.003

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Theoretical calculations using the DFT theory at the B3LYP/6-311++G** level were used to determine the molecular geometry of various glycosaminoglycan (GAG) molecules. Three-bond proton-proton spin-spin coupling constants ((3)J(H-C-C-H)) were then computed and compared with the published experimental data of selected mono- and disaccharides. The computed (3)J(H-C-C-H) values showed a strong dependence on the molecular geometry and varied up to 12 Hz. This dependence was expressed in a simple analytical form relating (3)J(H-C-C-H) and torsion angles. The population of conformers in heparin and other biologically active GAGS has also been estimated using the computed coupling constants. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：779 / 783

页数：5

共 24 条

[1] A molecular dynamics description of the conformational flexibility of the L-iduronate ring in glycosaminoglycans [J].

Angulo, J ;

Nieto, PM ;

Martín-Lomas, M .

CHEMICAL COMMUNICATIONS, 2003, (13) :1512-1513

[2]

[Anonymous], 2004, GAUSSIAN 03 REVISION

[3] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR [J].

BECKE, AD .

PHYSICAL REVIEW A, 1988, 38 (06) :3098-3100

[4] Conformational flexibility of a synthetic glycosylaminoglycan bound to a fibroblast growth factor.: FGF-1 recognizes both the 1C4 and 2S0 conformations of a bioactive heparin-like hexasaccharide [J].

Canales, A ;

Angulo, J ;

Ojeda, R ;

Bruix, M ;

Fayos, R ;

Lozano, R ;

Giménez-Gallego, G ;

Martín-Lomas, M ;

Nieto, PM ;

Jiménez-Barbero, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5778-5779

[5]

Capila I, 2002, ANGEW CHEM INT EDIT, V41, P391

[6] Structure and biological interactions of heparin and heparan sulfate [J].

Casu, B ;

Lindahl, U .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, VOL 57, 2001, 57 :159-206

[7]

Conrad H.E., 1998, HEPARIN BINDING PROT

[8] Pyranose ring flexibility. Mapping of physical data for iduronate in continuous conformational space [J].

Ernst, S ;

Venkataraman, G ;

Sasisekharan, V ;

Langer, R ;

Cooney, CL ;

Sasisekharan, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (09) :2099-2107

[9] EVIDENCE FOR CONFORMATIONAL EQUILIBRIUM OF THE SULFATED L-IDURONATE RESIDUE IN HEPARIN AND IN SYNTHETIC HEPARIN MONOSACCHARIDES AND OLIGOSACCHARIDES - NMR AND FORCE-FIELD STUDIES [J].

FERRO, DR ;

PROVASOLI, A ;

RAGAZZI, M ;

TORRI, G ;

CASU, B ;

GATTI, G ;

JACQUINET, JC ;

SINAY, P ;

PETITOU, M ;

CHOAY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6773-6778

[10] CONFORMER POPULATIONS OF L-IDURONIC ACID RESIDUES IN GLYCOSAMINOGLYCAN SEQUENCES [J].

FERRO, DR ;

PROVASOLI, A ;

RAGAZZI, M ;

CASU, B ;

TORRI, G ;

BOSSENNEC, V ;

PERLY, B ;

SINAY, P ;

PETITOU, M ;

CHOAY, J .

CARBOHYDRATE RESEARCH, 1990, 195 (02) :157-167

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