NEW ACYCLIC ANALOGS OF LIPID-A - SYNTHESIS OF 4-PHOSPHONOXYBUTYL AND 3-PHOSPHONOXYPROPYL GLYCOSIDES OF 2-AMINO-2-DEOXY-D-GLUCOSE

被引：12

作者：

EUSTACHE, J

GROB, A

RETSCHER, H

机构：

[1] Sandoz Forschungsinstitut Wien, A-1235 Wien

来源：

CARBOHYDRATE RESEARCH | 1994年 / 251卷

关键词：

D O I：

10.1016/0008-6215(94)84290-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 [生物化学与分子生物学]; 081704 [应用化学];

摘要：

Several analogues of lipid A have been synthesized, in which the reducing monosaccharide moiety of the parent molecule has been replaced by an acyclic spacer. The new compounds show high endotoxic activity and are able to protect neutropenic mice against pseudomonas infection, two properties characteristic of LPS-like molecules.

引用

收藏

页码：251 / 267

页数：17

相关论文

共 24 条

[1]

Syntheses with glucosamine. [J].

Bergmann, M ;

Zervas, L .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1931, 64 :975-980

[2]

BLIGH EG, 1959, CAN J BIOCHEM PHYS, V37, P911

[3]

EFFECT OF MONOPHOSPHORYL LIPID-A ON HOST-RESISTANCE TO BACTERIAL-INFECTION [J].

CHASE, JJ ;

KUBEY, W ;

DULEK, MH ;

HOLMES, CJ ;

SALIT, MG ;

PEARSON, FC ;

RIBI, E .

INFECTION AND IMMUNITY, 1986, 53 (03) :711-712

[4]

GALACTOSAMINE-INDUCED SENSITIZATION TO THE LETHAL EFFECTS OF ENDOTOXIN [J].

GALANOS, C ;

FREUDENBERG, MA ;

REUTTER, W .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (11) :5939-5943

[5]

TOTAL SYNTHESIS OF ESCHERICHIA-COLI LIPID-A [J].

IMOTO, M ;

YOSHIMURA, H ;

SAKAGUCHI, N ;

KUSUMOTO, S ;

SHIBA, T .

TETRAHEDRON LETTERS, 1985, 26 (12) :1545-1548

[6]

CHEMICAL SYNTHESIS OF A BIOSYNTHETIC PRECURSOR OF LIPID-A WITH A PHOSPHORYLATED TETRAACYL DISACCHARIDE STRUCTURE [J].

IMOTO, M ;

YOSHIMURA, H ;

YAMAMOTO, M ;

SHIMAMOTO, T ;

KUSUMOTO, S ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2197-2204

[7]

SYNTHETIC APPROACH TO LIPID-A - PREPARATION OF PHOSPHORYLATED DISACCHARIDES CONTAINING (R)-3-HYDROXYACYL AND (R)-3-ACYLOXYACYL GROUPS [J].

INAGE, M ;

CHAKI, H ;

IMOTO, M ;

SHIMAMOTO, T ;

KUSUMOTO, S ;

SHIBA, T .

TETRAHEDRON LETTERS, 1983, 24 (19) :2011-2014

[8]

A CONVENIENT PREPARATIVE METHOD OF CARBOHYDRATE PHOSPHATES WITH BUTYLLITHIUM AND PHOSPHOROCHLORIDATE [J].

INAGE, M ;

CHAKI, H ;

KUSUMOTO, S ;

SHIBA, T .

CHEMISTRY LETTERS, 1982, (08) :1281-1284

[9]

NUCLEOTIDES .17. N-CHLOROAMIDES AS REAGENTS FOR THE CHLORINATION OF DIESTERS OF PHOSPHOROUS ACID - A NEW SYNTHESIS OF URIDINE-5' PYROPHOSPHATE [J].

KENNER, GW ;

TODD, AR ;

WEYMOUTH, FJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (OCT) :3675-3681

[10]

SYNTHESIS OF DISACCHARIDES BY THE FERRIC CHLORIDE-CATALYZED COUPLING OF 2-ACYLAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE 1-ACETATES TO PROTECTED SUGAR ACCEPTORS [J].

KISO, M ;

ANDERSON, L .

CARBOHYDRATE RESEARCH, 1979, 72 (JUL) :C15-C17