Structural analysis of two glycosphingolipids from the lipopolysaccharide-lacking bacterium Sphingomonas capsulata

被引：102

作者：

Kawahara, K

Moll, H

Knirel, YA

Seydel, U

Zähringer, U

机构：

[1] Forschungszentrum Borstel, Zentrum Med & Biowissensch, D-23845 Borstel, Germany

[2] Kitasato Inst, Dept Bacteriol, Tokyo 108, Japan

[3] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow, Russia

来源：

EUROPEAN JOURNAL OF BIOCHEMISTRY | 2000年 / 267卷 / 06期

关键词：

chemical structure; glycosphingolipids; Sphingomonas capsulata; lipopolysaccharide-free Gram-negative bacteria;

D O I：

10.1046/j.1432-1327.2000.01189.x

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：

Two glycosphingolipids, GSL-1 and GSL-3, were isolated from Sphingomonas capsulata and studied by methylation analysis, laser desorption mass spectrometry, and H-1 and C-13 NMR spectroscopy, including two-dimensional H-1,H-1 COSY and heteronuclear C-13,H-1 COSY experiments. GSL-1 and GSL-3 differ in their carbohydrate part, their structures being alpha-d-GlcpA-(1 --> 1)-Cer and alpha-d-Galp-(1 --> 6)-alpha-D-GlcpN-(1 --> 4)-alpha-D-GlcpA(1 --> 1)Cer, respectively. Variations occur in the ceramide of GSL-1 and GSL-3, both having the same long-chain bases, erythro-2-amino-1,3-octadecanediol (sphinganine), (13Z)-erythro-2-amino-13-eicosene-1,3-diol and (13Z)-erythro-2-amino-13,14-methylene-1,3-eicosanediol, in the ratios 2.6 : 1 : 3.5 in GSL-1 and 1 : 1.2 : 1.5 in GSL-3. All bases are quantitatively substituted by amide-linked (S)-2-hydroxymyristic acid.

引用

页码：1837 / 1846

页数：10

共 38 条

[1]

[Anonymous], 1988, Microbial Lipids

[2] Taxonomic study of aromatic-degrading bacteria from deep-terrestrial-subsurface sediments and description of Sphingomonas aromaticivorans sp nov, Sphingomonas subterranea sp nov, and Sphingomonas stygia sp nov [J].

Balkwill, DL ;

Drake, GR ;

Reeves, RH ;

Fredrickson, JK ;

White, DC ;

Ringelberg, DB ;

Chandler, DP ;

Romine, MF ;

Kennedy, DW ;

Spadoni, CM .

INTERNATIONAL JOURNAL OF SYSTEMATIC BACTERIOLOGY, 1997, 47 (01) :191-201

[3] A novel glycosphingolipid from Gram-negative aquatic bacteria [J].

Batrakov, SG ;

Sheichenko, VI ;

Nikitin, DI .

BIOCHIMICA ET BIOPHYSICA ACTA-MOLECULAR AND CELL BIOLOGY OF LIPIDS, 1999, 1440 (2-3) :163-175

[4] A MODIFIED URONIC ACID CARBAZOLE REACTION [J].

BITTER, T ;

MUIR, HM .

ANALYTICAL BIOCHEMISTRY, 1962, 4 (04) :330-&

[5] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES [J].

BOCK, K ;

PEDERSEN, C .

ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 :27-66

[6]

BRAUN PE, 1970, J BIOL CHEM, V245, P335

[7]

BRAUN PE, 1968, J BIOL CHEM, V243, P3775

[8]

GUNSTONE FD, 1993, ADV LIPID METHODOLOG, V2, P1

[9] LIPOPOLYSACCHARIDE (LPS)-BINDING PROTEIN ACCELERATES THE BINDING OF LPS TO CD14 [J].

HAILMAN, E ;

LICHENSTEIN, HS ;

WURFEL, MM ;

MILLER, DS ;

JOHNSON, DA ;

KELLEY, M ;

BUSSE, LA ;

ZUKOWSKI, MM ;

WRIGHT, SD .

JOURNAL OF EXPERIMENTAL MEDICINE, 1994, 179 (01) :269-277

[10]

HAKOMORI SI, 1964, J BIOCHEM-TOKYO, V55, P205

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