Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides

被引:60
作者
Baeschlin, DK [1 ]
Green, LG [1 ]
Hahn, MG [1 ]
Hinzen, B [1 ]
Ince, SJ [1 ]
Ley, SV [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
基金
英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;
关键词
D O I
10.1016/S0957-4166(99)00519-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
This paper describes the application of 1,2-diacetal protecting groups to control the reactivity tuning of glycosyl fluorides in oligosaccharide coupling reactions. The synthetic potential of this new methodology is demonstrated by the 'one-pot' synthesis of a linear pentasaccharide and the efficient assembly of the core oligosaccharide of the GPI anchor of yeast (Saccharomyces cerevisiae). (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:173 / 197
页数:25
相关论文
共 85 条
[71]   Alternative lipid remodelling pathways for glycosylphosphatidylinositol membrane anchors in Saccharomyces cerevisiae [J].
Sipos, G ;
Reggiori, F ;
Vionnet, C ;
Conzelmann, A .
EMBO JOURNAL, 1997, 16 (12) :3494-3505
[72]  
Stepanov AE, 1998, BIOORG KHIM+, V24, P731
[73]   NEW METHODS IN GLYCOSIDE SYNTHESIS BY USING EARLY TRANSITION-METAL DERIVED REAGENT [J].
SUZUKI, K ;
MATSUMOTO, T .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1993, 51 (08) :718-732
[74]   Synthesis of the glycosyl phosphatidyl inositol anchor of rat brain Thy1 [J].
Tailler, D ;
Ferrières, V ;
Pekari, K ;
Schmidt, RR .
TETRAHEDRON LETTERS, 1999, 40 (04) :679-682
[75]   Biosynthesis of glycosylphosphatidylinositols in mammals and unicellular microbes [J].
Tiede, A ;
Bastisch, I ;
Schubert, J ;
Orlean, P ;
Schmidt, RE .
BIOLOGICAL CHEMISTRY, 1999, 380 (05) :503-523
[76]   RECENT PROGRESS IN O-GLYCOSYLATION METHODS AND ITS APPLICATION TO NATURAL-PRODUCTS SYNTHESIS [J].
TOSHIMA, K ;
TATSUTA, K .
CHEMICAL REVIEWS, 1993, 93 (04) :1503-1531
[77]   AN EFFICIENT THIOGLYCOSIDE-MEDIATED FORMATION OF ALPHA-GLYCOSIDIC LINKAGES PROMOTED BY IODONIUM DICOLLIDINE PERCHLORATE [J].
VEENEMAN, GH ;
VANBOOM, JH .
TETRAHEDRON LETTERS, 1990, 31 (02) :275-278
[78]   IODONIUM ION PROMOTED REACTIONS AT THE ANOMERIC CENTER .2. AN EFFICIENT THIOGLYCOSIDE MEDIATED APPROACH TOWARD THE FORMATION OF 1,2-TRANS LINKED GLYCOSIDES AND GLYCOSIDIC ESTERS [J].
VEENEMAN, GH ;
VANLEEUWEN, SH ;
VANBOOM, JH .
TETRAHEDRON LETTERS, 1990, 31 (09) :1331-1334
[79]  
VERDUYN R, 1990, RECL TRAV CHIM PAY B, V109, P591
[80]  
WATTS C, 1999, THESIS U CAMBRIDGE