SYNTHESIS OF ALLYL 6-O-(3-DEOXY-ALPHA-D-MANNO-OCT-2-ULOPYRANOSYLONIC ACID AND 3-DEOXY-BETA-D-MANNO-OCT-2-ULOPYRANOSYLONIC ACID)-(1-]6)-2-DEOXY-2-[(3R)-3-HYDROXYTETRADECANAMIDO]-BETA-D-GLUCOPYRANOSIDE 4-PHOSPHATE AND OF THE COPOLYMER OF THE ALPHA ANOMER WITH ACRYLAMIDE

被引:5
作者
AUZANNEAU, FI [1 ]
MONDANGE, M [1 ]
CHARON, D [1 ]
SZABO, L [1 ]
机构
[1] UNIV PARIS 11, CTR ETUD PHARMACEUT,CNRS,URA 1116, EQUIPE ENDOTOXINES, F-92290 CHATENAY MALABRY, FRANCE
关键词
D O I
10.1016/S0008-6215(00)90547-0
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 title disaccharides were synthesized by mercuric cyanide-catalyzed condensation of methyl (4,5,7,8-tetra-O-acetyl-3-deoxy-alpha-D-manno-oct-2-ulopyranosyl bromide)onate and allyl 2-[(3 R)-3-acetoxy-tetradecanamido]-3-O-benzyl-2-deoxy-beta-D-glucopyranoside, followed by phosphorylation of the alcoholic function of the amino sugar. The phosphorylated anomers were separated by chromatography and deprotected by conventional methods. Polymeric material was obtained by copolymerisation, catalyzed by peroxosulphate and N,N,N',N"-tetramethylethylenediamine, of the alpha anomer with acrylamide; it contained ca. one disaccharide unit for 18 acrylamide residues.
引用
收藏
页码:37 / 45
页数:9
相关论文
共 30 条
[1]   CHEMISTRY OF BACTERIAL-ENDOTOXINS .2. A PRACTICAL SYNTHESIS OF 6-O-(4-O-AMMONIO(HYDROGEN)PHOSPHONO-2-DEOXY-2-[(3R)-3-HYDROXYTETRADECANAMIDO]-BETA-D-GLUCOPYRANOSYL)-2-DEOXY-2-[(3R)-3-HYDROXYTETRADECANAMIDO]-D-GLUCOSE [J].
CHARON, D ;
MONDANGE, M ;
SZABO, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (10) :2291-2295
[2]   PYRANOSIDE DERIVATIVES OF 3-DEOXYALD-2-ULOSONIC ACIDS [J].
CHARON, D ;
SZABO, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1971-1977
[3]   THE STRUCTURE OF 3-DEOXYOCTULOSONIC ACID (KDO) REGION OF LIPOPOLYSACCHARIDES OF SALMONELLA-MINNESOTA RE-595 [J].
CHRISTIAN, R ;
SCHULZ, G ;
WALDSTATTEN, P ;
UNGER, FM .
TETRAHEDRON LETTERS, 1984, 25 (32) :3433-3436
[4]   SYNTHESIS OF ALPHA,BETA-UNSATURATED ANALOGS OF KDO AND N-ACETYLNEURAMINIC ACID BY TRIMETHYLSILYL TRIFLATE-CATALYZED ELIMINATION-REACTIONS [J].
CLAESSON, A ;
LUTHMAN, K .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1982, 36 (10) :719-720
[5]   SYNTHESIS OF TYPE-2 HUMAN BLOOD-GROUP ANTIGENIC DETERMINANTS - THE H, X, AND Y-HAPTENS AND VARIATIONS OF THE H-TYPE-2 DETERMINANT AS PROBES FOR THE COMBINING SITE OF THE LECTIN-I OF ULEX-EUROPAEUS [J].
HINDSGAUL, O ;
NORBERG, T ;
LEPENDU, J ;
LEMIEUX, RU .
CARBOHYDRATE RESEARCH, 1982, 109 (NOV) :109-142
[6]   STUDIES ON LECTINS .35. WATER-SOLUBLE O-GLYCOSYL POLYACRYLAMIDE DERIVATIVES FOR SPECIFIC PRECIPITATION OF LECTINS [J].
HOREJSI, V ;
SMOLEK, P ;
KOCOUREK, J .
BIOCHIMICA ET BIOPHYSICA ACTA, 1978, 538 (02) :293-298
[7]  
HUET F, 1978, SYNTHESIS-STUTTGART, P63
[8]   DERIVATIZATION PROCEDURES FOR REDUCING OLIGOSACCHARIDES .3. PREPARATION OF OLIGOSACCHARIDE GLYCOSYLAMINES, AND THEIR CONVERSION INTO OLIGOSACCHARIDE-ACRYLAMIDE COPOLYMERS [J].
KALLIN, E ;
LONN, H ;
NORBERG, T ;
ELOFSSON, M .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (04) :597-611
[9]   CONJUGATES OF BIOLOGICALLY-ACTIVE LIPID-A-SUBUNIT ANALOGS WITH 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) AND ITS METHYL-ESTER [J].
KISO, M ;
FUJITA, M ;
TANAHASHI, M ;
FUJISHIMA, Y ;
OGAWA, Y ;
HASEGAWA, A ;
UNGER, FM .
CARBOHYDRATE RESEARCH, 1988, 177 :51-67
[10]   6-O-GLYCOSYLATION OF A LIPID A-SUBUNIT ANALOG (GLA-27) WITH METHYL (4,5,7,8-TETRA-O-ACETYL-3-DEOXY-ALPHA-D-MANNO-2-OCTULOPYRANOSYL BROMIDE)ONATE (A KDO DERIVATIVE) [J].
KISO, M ;
TANAHASHI, M ;
HASEGAWA, A ;
UNGER, FM .
CARBOHYDRATE RESEARCH, 1987, 163 (02) :279-284