Synthesis and anomeric stability of (1→6)-thiourea-linked pseudooligosaccharides

被引:37
作者
Benito, JM
Mellet, CO
Sadalapure, K
Lindhorst, TK
Defaye, J
Fernández, JMG
机构
[1] CSIC, Inst Invest Quim, E-41092 Seville, Spain
[2] Univ Seville, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain
[3] Univ Hamburg, Inst Organ Chem, D-20416 Hamburg, Germany
[4] CNRS, EP 811, Dept Pharmacochim Mol Glucides, F-38243 Meylan, France
[5] Univ Grenoble 1, F-38243 Meylan, France
关键词
sugar thioureas; sugar isothiocyanates; carbohydrate mimics; oligosaccharide mimics; anomerization;
D O I
10.1016/S0008-6215(99)00141-X
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
The synthesis of oligosaccharide mimics incorporating a thiourea intersaccharide bridge by coupling of mono- and disaccharide per-O-acetylated glycosyl isothiocyanates and methyl 6-amino-6-deoxy-alpha-D-glucopyranoside, is reported. An unexpected anomerization reaction was observed, however, for alpha- and beta-D-mannopyranosylthioureido derivatives upon Zemplen deacetylation. Kinetics studies revealed that this anomerization process is base catalysed and strongly dependent upon reaction temperature and reaction time. The fully unprotected compounds could be obtained without epimerization by performing the last step at 0 degrees C. In all cases, the final pseudooligosaccharides were stable in water solution at room temperature in the absence of base. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
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页码:37 / 48
页数:12
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