Synthesis and bioactivity of a fluorescence-labeled lipid A analogue

被引：9

作者：

Oikawa, M ^{[1
]}

Furuta, H ^{[1
]}

Suda, Y ^{[1
]}

Kusumoto, S ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 28期

基金：

日本学术振兴会;

关键词：

lipopolysaccharide; lipid A; fluorescence; biologically active compounds;

D O I：

10.1016/S0040-4039(99)00937-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A fluorescence-labeled phosphonooxyethyl (PE) analogue of lipid A has been successfully synthesized in 15 steps from D-glucosamine derivative 2 in total 16% yield. The analogue exhibits Limulus activity and cytokine-inducing activity similar to the natural lipopolysaccharide and the unlabeled PE analogue of lipid A. (C) 1999 Elsevier Science Ltd. All rights reserved.

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收藏

页码：5199 / 5202

页数：4

相关论文

共 14 条

[1] TOTAL SYNTHESIS OF THE PROPOSED STRUCTURE OF RHODOBACTER-SPHAEROIDES LIPID-A RESULTING IN SYNTHESIS OF NEW POTENT LIPOPOLYSACCHARIDE ANTAGONISTS [J].

CHRIST, WJ ;

MCGUINNESS, PD ;

ASANO, O ;

WANG, Y ;

MULLARKEY, MA ;

PEREZ, M ;

HAWKINS, LD ;

BLYTHE, TA ;

DUBUC, GR ;

ROBIDOUX, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (08) :3637-3638

[2] THE ALLYLOXYCARBONYL GROUP FOR ALCOHOL PROTECTION - QUANTITATIVE REMOVAL OR TRANSFORMATION INTO ALLYL PROTECTING GROUP VIA PI-ALLYL COMPLEXES OF PALLADIUM [J].

GUIBE, F ;

SAINTMLEUX, Y .

TETRAHEDRON LETTERS, 1981, 22 (37) :3591-3594

[3] 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

[4]

LIU W, IN PRESS

[5]

LIU WC, IN PRESS B CHEM SOC

[6] New efficient synthesis of a biosynthetic precursor of lipid A [J].

Oikawa, M ;

Wada, A ;

Yoshizaki, H ;

Fukase, K ;

Kusumoto, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (06) :1435-1440

[7] ON A PRACTICAL SYNTHESIS OF BETA-HYDROXY FATTY-ACID DERIVATIVES [J].

OIKAWA, M ;

KUSUMOTO, S .

TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :961-966

[8]

OIKAWA M, IN PRESS B CHEM SOC

[9]

OLTVOORT JJ, 1981, SYNTHESIS-STUTTGART, P305

[10] BACTERIAL, ENDOTOXIN - MOLECULAR RELATIONSHIPS OF STRUCTURE TO ACTIVITY AND FUNCTION [J].

RIETSCHEL, ET ;

KIRIKAE, T ;

SCHADE, FU ;

MAMAT, U ;

SCHMIDT, G ;

LOPPNOW, H ;

ULMER, AJ ;

ZAHRINGER, U ;

SEYDEL, U ;

DIPADOVA, F ;

SCHREIER, M ;

BRADE, H .

FASEB JOURNAL, 1994, 8 (02) :217-225