Complete 1H and 13C NMR chemical shift assignments of mono- to tetrasaccharides as basis for NMR chemical shift predictions of oligosaccharides using the computer program CASPER

被引:47
作者
Ronnols, Jerk [1 ]
Pendrill, Robert [1 ]
Fontana, Carolina [1 ]
Hamark, Christoffer [1 ]
d'Ortoli, Thibault Angles [1 ]
Engstrom, Olof [1 ]
Stahle, Jonas [1 ]
Zaccheus, Mona V. [1 ]
Sawen, Elin [1 ]
Hahn, Liljan E. [1 ]
Iqbal, Shahzad [1 ]
Widmalm, Goran [1 ]
机构
[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden
基金
瑞典研究理事会;
关键词
Oligosaccharide; Glycan; Chemical shift prediction; Automation; TREHALOSE-CONTAINING LIPOOLIGOSACCHARIDES; ACETYL-NEURAMINIC ACID; N-ACETYLGLUCOSAMINE; BLOOD-GROUP; LEWIS-X; CONFORMATIONAL PROPERTIES; CHEMOENZYMATIC SYNTHESIS; TRISACCHARIDE ANALOGS; STRUCTURAL-ANALYSIS; MASS-SPECTROMETRY;
D O I
10.1016/j.carres.2013.06.026
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
H-1 and C-13 NMR chemical shift data are used by the computer program CASPER to predict chemical shifts of oligo- and polysaccharides. Three types of data are used, namely, those from monosaccharides, disaccharides, and trisaccharides. To improve the accuracy of these predictions we have assigned the H-1 and C-13 NMR chemical shifts of eleven monosaccharides, eleven disaccharides, twenty trisaccharides, and one tetrasaccharide; in total 43 compounds. Five of the oligosaccharides gave two distinct sets of NMR resonances due to the alpha- and beta-anomeric forms resulting in 48 H-1 and C-13 NMR chemical shift data sets. In addition, the pyranose ring forms of Neu5Ac were assigned at two temperatures, due to chemical shift displacements as a function of temperature. The H-1 NMR chemical shifts were refined using total line-shape analysis with the PERCH NMR software. H-1 and C-13 NMR chemical shift predictions were subsequently carried out by the CASPER program (http://www.casper.organ.su.se/casper/) for three branched oligosaccharides having different functional groups at their reducing ends, namely, a mannose-containing pentasaccharide, and two fucose-containing heptasaccharides having N-acetyllactosamine residues in the backbone of their structures. Good to excellent agreement was observed between predicted and experimental H-1 and C-13 NMR chemical shifts showing the utility of the method for structural determination or confirmation of synthesized oligosaccharides. (C) 2013 Published by Elsevier Ltd.
引用
收藏
页码:156 / 166
页数:11
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