A convenient and efficient synthesis of sialyl Lewis X

被引:3
作者
Baba, K
Iwata, N
Hamajima, H
Ikami, T
Ishida, H
Hasegawa, A
Kiso, M
机构
[1] Sanwa Kagaku Kenkyusho Co Ltd, Drug Discovery Res Lab, Hokusei, Mie 51104, Japan
[2] Gifu Univ, Dept Appl Bioorgan Chem, Gifu 50111, Japan
关键词
selectin; glycosylation; sialyl Lewis X;
D O I
10.1271/bbb.62.590
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
a convenient synthesis of the sialyl Lewis X (sLe(x)) tetrasaccharide, NeuAc alpha 2-3Gal beta 1-4(Fuc alpha 1-3)GlcNac (8), as a carbohydrate ligand for selectins is described. The key step is the reaction between NeuAc alpha 2-3GalSMe (5) as a glycosyl donor and the suitably protected Fuc alpha 1-3GlcNac derivative (4) as the glycosyl acceptor by using dimethyl(methylthio)sulfonium triflate (DMTST) as the promoter.
引用
收藏
页码:590 / 592
页数:3
相关论文
共 18 条
[1]   THE 3 MEMBERS OF THE SELECTIN RECEPTOR FAMILY RECOGNIZE A COMMON CARBOHYDRATE EPITOPE, THE SIALYL LEWIS OLIGOSACCHARIDE [J].
FOXALL, C ;
WATSON, SR ;
DOWBENKO, D ;
FENNIE, C ;
LASKY, LA ;
KISO, M ;
HASEGAWA, A ;
ASA, D ;
BRANDLEY, BK .
JOURNAL OF CELL BIOLOGY, 1992, 117 (04) :895-902
[2]   A NOVEL PROMOTER FOR THE EFFICIENT CONSTRUCTION OF 1,2-TRANS LINKAGES IN GLYCOSIDE SYNTHESIS, USING THIOGLYCOSIDES AS GLYCOSYL DONORS [J].
FUGEDI, P ;
GAREGG, PJ .
CARBOHYDRATE RESEARCH, 1986, 149 (01) :C9-C12
[3]   OPTICALLY PURE N-SUBSTITUTED DERIVATIVES OF BENZYL 2-AMINO-2-DEOXY-ALPHA- AND -BETA-D-GLUCOPYRANOSIDE [J].
GROSS, PH ;
JEANLOZ, RW .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (09) :2759-&
[4]   SYNTHESIS OF SIALYL-LEWIS-X GANGLIOSIDE ANALOGS CONTAINING MODIFIED L-FUCOSE RESIDUES [J].
HASEGAWA, A ;
KATO, M ;
ANDO, T ;
ISHIDA, H ;
KISO, M .
CARBOHYDRATE RESEARCH, 1995, 274 :165-181
[5]   SYNTHETIC STUDIES ON SIALOGLYCO-CONJUGATES .67. SYNTHESIS OF A SIALYL-LEWIS-X GANGLIOSIDE ANALOG CONTAINING N-GLYCOLYL IN-PLACE OF THE N-ACETYL GROUP IN THE N-ACETYLNEURAMINIC ACID RESIDUE [J].
HASEGAWA, A ;
UCHIMURA, A ;
ISHIDA, H ;
KISO, M .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (06) :1091-1094
[6]   Synthetic studies on selectin ligands/inhibitors: One-pot synthesis of the mono- and oligo-sulfated 2-(tetradecyl)hexadecyl beta-D-galacto- and lactopyranosides as the sulfatide mimetics [J].
Ikami, T ;
Hamajima, H ;
Usui, T ;
Mitani, T ;
Ishida, H ;
Kiso, M ;
Hasegawa, A .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1997, 16 (06) :859-875
[7]   TOTAL SYNTHESIS OF 3'-O-SIALYL, 6'-O-SULFO LEWIS(X), NEUAC-ALPHA-2-]3(6-O-SO3NA)GA1-BETA-1-]4(FUC-ALPHA-1-]3)-GLCNAC-BETA-OME - A MAJOR CAPPING GROUP OF GLYCAM-I [J].
JAIN, RK ;
VIG, R ;
RAMPAL, R ;
CHANDRASEKARAN, EV ;
MATTA, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12123-12124
[8]   SYNTHETIC STUDIES ON SIALOGLYCOCONJUGATES .21. TOTAL SYNTHESIS OF SIALYL LEWIS-X [J].
KAMEYAMA, A ;
ISHIDA, H ;
KISO, M ;
HASEGAWA, A .
CARBOHYDRATE RESEARCH, 1991, 209 :C1-C4
[9]   SYNTHETIC STUDIES ON SIALYLGLYCOCONJUGATES .13. STEREOSELECTIVE SYNTHESIS OF SIALYL-LACTOTETRAOSYLCERAMIDE AND SIALYLNEOLACTOTETRAOSYLCERAMIDE [J].
KAMEYAMA, A ;
ISHIDA, H ;
KISO, M ;
HASEGAWA, A .
CARBOHYDRATE RESEARCH, 1990, 200 :269-285
[10]  
Kiso M, 1994, Bioorg Med Chem, V2, P1295, DOI 10.1016/S0968-0896(00)82080-5