CONFORMATIONAL MOBILITY OF OLIGOSACCHARIDES - EXPERIMENTAL-EVIDENCE FOR THE EXISTENCE OF AN ANTI CONFORMER OF THE GA1-BETA-1-3GLC-BETA-1-OME DISACCHARIDE

被引：75
作者：
DABROWSKI, J
KOZAR, T
GROSSKURTH, H
NIFANTEV, NE
机构：
[1] Max Planck Institute for Medical Research
[2] Institute of Experimental Physics, Slovak Academy of Sciences, Košice
[3] Zelinsky Institute of Organic Chemistry, Moscow
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 20期
关键词：
D O I：
10.1021/ja00125a015
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A hydrogen bond between the Glc OH(4) and Gal OH(2) groups of the title disaccharide, manifested by the doubling of their H-1 NMR signals in a partially deuteriated sample in Me(2)SO solution, proves the existence of an ''anti'' conformer, i.e., one with the anomeric and transglycosidic aglyconic C-H bonds turned away from each other by similar to 180 degrees. This conformer is at equilibrium with the predominating normal ''syn'' conformation(s), as shown by the analysis of several interresidue NOEs, and confirmed by molecular mechanics and molecular dynamics calculations.
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页码：5534 / 5539
页数：6
相关论文
共 56 条
[41]  
PAULSEN H, 1985, LIEBIGS ANN CHEM, P489
[42]   CONFORMATION OF THE GLYCOLIPID GLOBOSIDE HEAD GROUP IN VARIOUS SOLVENTS AND IN THE MICELLE-BOUND STATE [J].
POPPE, L ;
VONDERLIETH, CW ;
DABROWSKI, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7762-7771
[43]  
RAMBAUD E, 1992, CARBOHYD RES, V227, P351
[44]   IMPROVED TECHNIQUES FOR HOMONUCLEAR ROTATING-FRAME AND ISOTROPIC MIXING EXPERIMENTS [J].
RANCE, M .
JOURNAL OF MAGNETIC RESONANCE, 1987, 74 (03) :557-564
[45]   ISOTOPIC MULTIPLETS IN THE C-13-NMR SPECTRA OF POLYOLS WITH PARTIALLY DEUTERATED HYDROXYLS .3. FINGERPRINTS OF MOLECULAR-STRUCTURE AND HYDROGEN-BONDING EFFECTS IN THE C-13-NMR SPECTRA OF MONOSACCHARIDES WITH PARTIALLY DEUTERATED HYDROXYLS [J].
REUBEN, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (21) :6180-6186
[46]   CHARACTERIZATION OF THE EXTENT OF INTERNAL MOTIONS IN OLIGOSACCHARIDES [J].
RUTHERFORD, TJ ;
PARTRIDGE, J ;
WELLER, CT ;
HOMANS, SW .
BIOCHEMISTRY, 1993, 32 (47) :12715-12724
[47]   NMR AND COMPUTATIONAL STUDIES OF INTERACTIONS BETWEEN REMOTE RESIDUES IN GANGLIOSIDES [J].
SCARSDALE, JN ;
PRESTEGARD, JH ;
YU, RK .
BIOCHEMISTRY, 1990, 29 (42) :9843-9855
[48]   H-1 AND C-13 NMR DATA FOR 2-O-DI-O-GLYCOSYLATED, 3-O-DI-O-GLYCOSYLATED AND 2,3-DI-O-GLYCOSYLATED METHYL ALPHA-D-GLUCOPYRANOSIDES AND BETA-D-GLUCOPYRANOSIDES AND BETA-D-GALACTOPYRANOSIDES [J].
SHASHKOV, AS ;
NIFANTEV, NE ;
AMOCHAEVA, VY ;
KOCHETKOV, NK .
MAGNETIC RESONANCE IN CHEMISTRY, 1993, 31 (06) :599-605
[49]   Z-FILTERS FOR PURGING PHASE-DISTORTED OR MULTIPLET-DISTORTED SPECTRA [J].
SORENSEN, OW ;
RANCE, M ;
ERNST, RR .
JOURNAL OF MAGNETIC RESONANCE, 1984, 56 (03) :527-534
[50]   MOLECULAR RECOGNITION .7. SYNTHETIC, CONFORMATIONAL, AND IMMUNOCHEMICAL STUDIES OF MODIFIED LEWIS-B AND Y-HUMAN BLOOD-GROUP DETERMINANTS TO SERVE AS PROBES FOR THE COMBINING SITE OF THE LECTIN-IV OF GRIFFONIA-SIMPLICIFOLIA [J].
SPOHR, U ;
LEMIEUX, RU .
CARBOHYDRATE RESEARCH, 1988, 174 :211-237
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