Chemoenzymatic synthesis of GM(3), Lewis x and sialyl Lewis x oligosaccharides in C-13-enriched form

被引:36
作者
Probert, MA
Milton, MJ
Harris, R
Schenkman, S
Brown, JM
Homans, SW
Field, RA
机构
[1] UNIV ST ANDREWS,SCH CHEM,ST ANDREWS KY16 9ST,FIFE,SCOTLAND
[2] UNIV ST ANDREWS,CTR BIOMOL SCI,ST ANDREWS KY16 9ST,FIFE,SCOTLAND
[3] UNIV FED SAO PAULO,ESCOLA PAULISTA MED,DEPT MICROBIOL IMUNOL & PARASITOL,BR-04023062 SAO PAULO,BRAZIL
[4] MARTEK BIOSCI CORP,COLUMBIA,MD 21045
基金
英国惠康基金;
关键词
D O I
10.1016/S0040-4039(97)01304-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In connection with studies on the solution and protein-bound conformation of oligosaccharides, we had reason to consider the application of C-13-enriched sugars. Herein we describe the synthesis of ganglioside GM(3) trisaccharide (1), Lewis x trisaccharide (2) and the sialyl Lewis x tetrasaccharide (3) from [U-C-13]-D-Glc, [U-C-13]-L-Gal and [U-C-13]-pyruvate. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:5861 / 5864
页数:4
相关论文
共 22 条
[1]   LARGE-SCALE SYNTHESIS OF BETA-L-FUCOPYRANOSYL PHOSPHATE AND THE PREPARATION OF GDP-BETA-L-FUCOSE [J].
ADELHORST, K ;
WHITESIDES, GM .
CARBOHYDRATE RESEARCH, 1993, 242 :69-76
[2]   A multigram, stereoselective synthesis of D-[C-13(5)]ribose from D-[C-13(6)]glucose and its conversion into [C-13(5)]nucleosides [J].
Agrofoglio, LA ;
Jacquinet, JC ;
Lancelot, G .
TETRAHEDRON LETTERS, 1997, 38 (08) :1411-1412
[3]   C-13-H-1 and C-13-C-13 spin couplings in [2'-C-13]2'-deoxyribonucleosides: Correlations with molecular structure [J].
Bandyopadhyay, T ;
Wu, J ;
Stripe, WA ;
Carmichael, I ;
Serianni, AS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1737-1744
[4]   MICROALGAE AS A SOURCE OF STABLE ISOTOPICALLY LABELED COMPOUNDS [J].
BEHRENS, PW ;
SICOTTE, VJ ;
DELENTE, J .
JOURNAL OF APPLIED PHYCOLOGY, 1994, 6 (02) :113-121
[5]   THE CONFORMATION OF THE SIALYL-LEWIS-X LIGAND CHANGES UPON BINDING TO E-SELECTIN [J].
COOKE, RM ;
HALE, RS ;
LISTER, SG ;
SHAH, G ;
WEIR, MP .
BIOCHEMISTRY, 1994, 33 (35) :10591-10596
[6]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[7]   Synthesis of C-13 enriched sialyllactones and their characterization using isotope edited inverse detected NMR spectroscopy [J].
Gervay, J ;
Mamuya, NN ;
Barber, RA .
TETRAHEDRON LETTERS, 1997, 38 (11) :1865-1868
[8]   REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .2. SCOPE AND SYNTHETIC UTILITY IN METHYL 4,6-O-BENZYLIDENEHEXOPYRANOSIDE SERIES [J].
HANESSIAN, S ;
PLESSAS, NR .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :1035-+
[9]   Three-dimensional heteronuclear NMR techniques for assignment and conformational analysis using exchangeable protons in uniformly C-13-enriched oligosaccharides [J].
Harris, R ;
Rutherford, TJ ;
Milton, MJ ;
Homans, SW .
JOURNAL OF BIOMOLECULAR NMR, 1997, 9 (01) :47-54
[10]   CONFORMATION AND DYNAMICS OF OLIGOSACCHARIDES IN SOLUTION [J].
HOMANS, SW .
GLYCOBIOLOGY, 1993, 3 (06) :551-555