Synthesis of sialyl Lewis X analogues

被引:10
作者
Dekany, G
Wright, K
Ward, P
Toth, I
机构
[1] UNIV LONDON,SCH PHARM,LONDON WC1N 1AX,ENGLAND
[2] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
关键词
D O I
10.1080/07328309608005661
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
Sialyl Lewis X (SLe(x)) analogs 2a and 2b were synthesised, where the N-acetyl-D-glucose and the D-galactose units of SLe(x) 1 were replaced with an alkyl and a heteroalkyl spacer. Sulphate ester 6i was also synthesised from alcohol 6b and chlorosulphonic acid. A novel promoter. silver mercaptoethanesulphonate. was used to synthesise alpha-sialosides 2c, 7b and 7c.
引用
收藏
页码:383 / 398
页数:16
相关论文
共 27 条
[1]   SYNTHESIS OF 1,2-CIS-LINKED GLYCOSIDES USING DIMETHYL(METHYLTHIO)SULFONIUM TRIFLATE AS PROMOTER AND THIOGLYCOSIDES AS GLYCOSYL DONORS [J].
ANDERSSON, F ;
FUGEDI, P ;
GAREGG, PJ ;
NASHED, M .
TETRAHEDRON LETTERS, 1986, 27 (33) :3919-3922
[2]   EFFICIENT CONVERSION OF THIOGLYCOSIDES INTO GLYCOSYL FLUORIDES USING DIMETHYL(METHYLTHIO)SULFONIUM TETRAFLUOROBORATE [J].
BLOMBERG, L ;
NORBERG, T .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (06) :751-760
[3]   NEW APPROACH TO THE SYNTHESIS OF 5-N-ACETYL-D-NEURAMINIC ACID ALPHA-KETOSIDES [J].
ESCHENFELDER, V ;
BROSSMER, R .
CARBOHYDRATE RESEARCH, 1980, 78 (01) :190-194
[4]  
HASEGAWA A, 1993, GLYCOCONJUGATE J, V10, P3
[5]   HIGH-RESOLUTION H-1-NMR SPECTROSCOPY OF FREE AND GLYCOSIDICALLY LINKED O-ACETYLATED SIALIC ACIDS [J].
HAVERKAMP, J ;
VANHALBEEK, H ;
DORLAND, L ;
VLIEGENTHART, JFG ;
PFEIL, R ;
SCHAUER, R .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1982, 122 (02) :305-311
[6]  
KANEYAMA A, 1991, J CARBOHYD CHEM, V10, P549
[7]   STUDIES ON THE THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID .5. GLYCOSYLATION USING METHYLTHIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID AND DIMETHYL(METHYLTHIO)SULFONIUM TRIFLATE [J].
KANIE, O ;
KISO, M ;
HASEGAWA, A .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (02) :501-506
[8]   SYNTHESE ANOMERER SIALINSAURE-METHYLKETOSIDE [J].
KUHN, R ;
LUTZ, P ;
MACDONALD, DL .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (02) :611-+
[9]  
LEMIEUX R, 1974, J AM CHEM SOC, V97, P4056
[10]   SYNTHESIS OF GLYCOSYLATED AMINO-ACIDS FOR USE IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS .2. N-(9-FLUORENYLMETHYLOXYCARBONYL)-3-O-[2,4,6-TRI-O-ACETYL-3-O-(2,3,4-TRI-O-ACETYL-ALPHA-D-XYLOPYRANOSYL)-BETA-D-GLUCOPYRANOSYL]-L-SERINE [J].
LUNING, B ;
NORBERG, T ;
TEJBRANT, J .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1992, 11 (07) :933-943