A divergent synthesis of lipid A and its chemically stable unnatural analogues

被引：58

作者：

Liu, WC ^{[1
]}

Oikawa, M ^{[1
]}

Fukase, K ^{[1
]}

Suda, Y ^{[1
]}

Kusumoto, S ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1999年 / 72卷 / 06期

关键词：

D O I：

10.1246/bcsj.72.1377

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lipid A and its two chemically stable analogues, wherein the glycosidic phosphoryl groups in lipid A is replaced with 2-(phosphonooxy)ethyl or carboxymethyl groups, have been synthesized by an improved and divergent route via a common allyl glycoside intermediate in which the 4-hydroxy group was protected as a benzyl ether. The total yields were more than 20% for 11 or 12 steps starting from allyl 4,6-O-benzylidene-2-deoxy-2- (trichloroethoxycarbonylamino)-D-glucopyranoside. These synthetic chemically stable analogues induce interleukin-6 and tumor necrosis factor alpha in human peripheral whole blood cells with potencies comparable to those by natural-type synthetic lipid A. The Limulus activities of both analogues were found to be even stronger than the activity of the natural-type one.

引用

页码：1377 / 1385

页数：9

共 20 条

[1] Divergent synthesis and biological activities of lipid A analogues of shorter acyl chains [J].

Fukase, K ;

Fukase, Y ;

Oikawa, M ;

Liu, WC ;

Suda, Y ;

Kusumoto, S .

TETRAHEDRON, 1998, 54 (16) :4033-4050

[2]

HEINE H, 1994, J ENDOTOXIN RES, V1, P14

[3] 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

[4] TOTAL SYNTHESIS OF ESCHERICHIA-COLI LIPID-A, THE ENDOTOXICALLY ACTIVE PRINCIPLE OF CELL-SURFACE LIPOPOLYSACCHARIDE [J].

IMOTO, M ;

YOSHIMURA, H ;

SHIMAMOTO, T ;

SAKAGUCHI, N ;

KUSUMOTO, S ;

SHIBA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) :2205-2214

[5] 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

[6] 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

[7] SYNTHETIC STUDIES TOWARD MARINE TOXIC POLYETHERS (5) THE TOTAL SYNTHESIS OF OKADAIC ACID [J].

ISOBE, M ;

ICHIKAWA, Y ;

GOTO, T .

TETRAHEDRON LETTERS, 1986, 27 (08) :963-966

[8]

KUSAMA T, 1991, CHEM PHARM BULL, V39, P3244

[9] SYNTHESIS AND ANTITUMOR-ACTIVITY OF LIPID-A ANALOGS HAVING A PHOSPHONOOXYETHYL GROUP WITH ALPHA-CONFIGURATION OR BETA-CONFIGURATION AT POSITION-1 [J].

KUSAMA, T ;

SOGA, T ;

SHIOYA, E ;

NAKAYAMA, K ;

NAKAJIMA, H ;

OSADA, Y ;

ONO, Y ;

KUSUMOTO, S ;

SHIBA, T .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3366-3372

[10] Enzymatic preparation of (S)-3-hydroxytetradecanoic acid and synthesis of unnatural analogues of lipid a containing the (S)-acid [J].

Liu, WC ;

Oikawa, M ;

Fukase, K ;

Suda, Y ;

Winarno, H ;

Mori, S ;

Hashimoto, M ;

Kusumoto, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (06) :1441-1450

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