Studies Related to Norway Spruce Galactoglucomannans: Chemical Synthesis, Conformation Analysis, NMR Spectroscopic Characterization, and Molecular Recognition of Model Compounds

被引:32
作者
Ekholm, Filip S. [1 ]
Arda, Ana [2 ]
Eklund, Patrik [1 ]
Andre, Sabine [3 ]
Gabius, Hans-Joachim [3 ]
Jimenez-Barbero, Jesus [2 ]
Leino, Reko [1 ]
机构
[1] Abo Akad Univ, Organ Chem Lab, SF-20500 Turku, Finland
[2] CSIC, Ctr Invest Biol, Madrid 28040, Spain
[3] Univ Munich, Fac Vet Med, Inst Physiol Chem, D-80539 Munich, Germany
基金
芬兰科学院;
关键词
conformation analysis; galactoglucomannan; molecular recognition; NMR spectroscopy; oligosaccharide synthesis; CARBOHYDRATE-PROTEIN INTERACTIONS; ACETYLATED GALACTOGLUCOMANNAN; 4,6-O-BENZYLIDENE ACETALS; THERMOMECHANICAL PULP; REDUCTIVE OPENINGS; MISTLETOE LECTIN; LIGAND-BINDING; PICEA-ABIES; POLYSACCHARIDES; GALACTOSYLATION;
D O I
10.1002/chem.201200510
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Galactoglucomannan (GGM) is a polysaccharide mainly consisting of mannose, glucose, and galactose. GGM is the most abundant hemicellulose in the Norway spruce (Picea abies), but is also found in the cell wall of flax seeds, tobacco plants, and kiwifruit. Although several applications for GGM polysaccharides have been developed in pulp and paper manufacturing and the food and medical industries, attempts to synthesize and study distinct fragments of this polysaccharide have not been reported previously. Herein, the synthesis of one of the core trisaccharide units of GGM together with a less-abundant tetrasaccharide fragment is described. In addition, detailed NMR spectroscopic characterization of the model compounds, comparison of the spectral data with natural GGM, investigation of the acetyl-group migration phenomena that takes place in the polysaccharide by using small model compounds, and a binding study between the tetrasaccharide model fragment and a galactose-binding protein (the toxin viscumin) are reported.
引用
收藏
页码:14392 / 14405
页数:14
相关论文
共 82 条
[1]   Synthesis of tethered trisaccharides to probe inter-saccharide flexibility in carbohydrate-protein interactions [J].
Alibés, R ;
Bundle, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (18) :6288-6301
[2]   MOLECULAR MECHANICS - THE MM3 FORCE-FIELD FOR HYDROCARBONS .1. [J].
ALLINGER, NL ;
YUH, YH ;
LII, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8551-8566
[3]  
ANNERGREN G.E., 1960, Sven. Papperstidn, V63, P591
[4]  
[Anonymous], SVENSK PAPPERSTIDNIN
[5]   N-pentenyl glycoside methodology in the stereoselective construction of the tetrasaccharyl cap portion of Leishmania lipophosphoglycan [J].
Arasappan, A ;
FraserReid, B .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2401-2406
[6]   Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides [J].
Baeschlin, DK ;
Green, LG ;
Hahn, MG ;
Hinzen, B ;
Ince, SJ ;
Ley, SV .
TETRAHEDRON-ASYMMETRY, 2000, 11 (01) :173-197
[7]   MLEV-17-BASED TWO-DIMENSIONAL HOMONUCLEAR MAGNETIZATION TRANSFER SPECTROSCOPY [J].
BAX, A ;
DAVIS, DG .
JOURNAL OF MAGNETIC RESONANCE, 1985, 65 (02) :355-360
[8]  
BERGER S, 1998, 200 MORE NMR EXPT, P488
[9]  
BOCK K, 1982, ANN REPORTS NMR SPEC, P2
[10]  
Bock K., 1974, J CHEM SOC, V2, P293