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Chemical Structure of Bacteriovorax stolpii Lipid A

  • Original Article
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Lipids

Abstract

Bdellovibrionales is a phylogenetically diverse group of predatory prokaryotes, which consists of the two families Bdellovibrionaceae and Bacteriovoracaceae. We describe LPS and lipid A of the type strain Bacteriovorax stolpii DSM 12778, representing the first characterized endotoxin of a Bacteriovoracaceae member. It has a smooth form LPS, which was identified by SDS-polyacrylamide gel electrophoresis. The lipid A structure was determined by combined gas chromatography–mass spectrometry, electrospray ionization mass spectrometry and NMR spectroscopy. Its backbone consists of two β-(1 → 6)-linked 2,3-diamino-2,3-dideoxy-d-glucopyranoses (GlcpN3N) carrying a pyrophosphoethanolamine at O-4′ of the non-reducing sugar and a phosphate group linked to O-1 of the reducing GlcpN3N. Positions 2, 3, 2′ and 3′ of the two GlcpN3N are acylated with primary 3-hydroxy fatty acids and one of those carries a secondary fatty acid.

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Abbreviations

BALOs:

Bdellovibrio-and-like organisms

CID:

Collision induced dissociation

COSY:

Correlation spectroscopy

ESI–MS:

Electrospray ionization–mass spectrometry

EXSY:

Exchange spectroscopy

FTICR MS:

Fourier transform ion cyclotron resonance mass spectrometry

GC–MS:

Gas chromatography–mass spectrometry

GlcpN3N:

2,3-diamino-2,3-dideoxy-d-glucopyranose

HMBC:

Heteronuclear multiple bond coherence

HMQC:

Heteronuclear multiple quantum coherence

LPS:

Lipopolysaccharide

MALDI-ToF:

Matrix assisted laser desorption/ionisation-time of flight mass spectrometry

NMR:

Nuclear magnetic resonance

NOESY:

Nuclear Overhauser effect spectroscopy

P I :

Phosphate residue at C-1 of the reducing sugar GlcpN3NI

P II :

Phosphate residue at C-4 of the non-reducing sugar GlcpN3NII

PEtN:

Phosphoethanolamine

R-form LPS:

Rough form lipopolysaccharide

ROESY:

Rotating frame nuclear Overhauser effect spectroscopy

SDS-PAGE:

Sodium dodecylsulfate polyacrylamide gel electrophoresis

S-form LPS:

Smooth form lipopolysaccharide

TOCSY:

Total correlation spectroscopy

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Acknowledgments

The authors gratefully acknowledge financial support by the Deutsche Forschungsgemeinschaft Grant LI309/29-1 (to F. M.).

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Authors and Affiliations

  1. Department of Chemistry, Humboldt-Universität zu Berlin, Brook-Taylor-Str. 2, 12489, Berlin, Germany

    Sebastian Beck, Frederic D. Müller & Michael W. Linscheid

  2. Department of Biological Safety, Federal Institute for Risk Assessment, Diedersdorfer Weg 1, 12277, Berlin, Germany

    Sebastian Beck, Frederic D. Müller & Eckhard Strauch

  3. Department of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria

    Lothar Brecker

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  1. Sebastian Beck
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  2. Frederic D. Müller
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  3. Eckhard Strauch
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  5. Michael W. Linscheid
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Corresponding author

Correspondence to Michael W. Linscheid.

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S. Beck and F. D. Müller contributed equally to this work.

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Beck, S., Müller, F.D., Strauch, E. et al. Chemical Structure of Bacteriovorax stolpii Lipid A. Lipids 45, 189–198 (2010). https://doi.org/10.1007/s11745-010-3383-6

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  • DOI: https://doi.org/10.1007/s11745-010-3383-6

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