Location of fatty acids in lipid A obtained from lipopolysaccharide of Rhodopseudomons sphaeroides ATCC 17023

N. Qureshi, J. P. Honovich, H. Hara, Robert J. Cotter, K. Takayama

Research output: Contribution to journalArticle

Abstract

Monophosphoryl lipid A (MLA) obtained from the lipopolysaccharide of Rhodopseudomonas sphaeroides ATCC 17023 was initially purified by silicic acid column chromatography to yield a single major pentaacyl MLA fraction. This fraction was methylated and further purified by reverse-phase high performance liquid chromtography to yield three prominent peak fractions. Laser desorption mass spectrometry of these three fractions allowed us to complete the important structural analysis of lipid A from this source. Three structurally distinct forms of dimethyl MLAwere identified where M(r) = 1447, 1449, and 1451 atomic mass units. These forms differed only by the presence or absence of unsaturation and keto group in the fatty acids. We established that the acyloxyacyl group (either Δ7-tetradecenoyloxytetradecanoate or tetradecanoyloxytetradecanoate) and the 3-ketotetradecanoate or hydroxytertadecanoate occupied the 2'- and 2-positions of the glucosamine disaccharide, respectively. Analysis of several minor fractions suggests that there is considerable structural heterogeneity in the MLA. With this new knowledge, the study of the structure-to-function relationship of the reported lack of toxicity of lipopolysaccharide from R. sphaeroides can be completed.

Original languageEnglish (US)
Pages (from-to)5502-5504
Number of pages3
JournalJournal of Biological Chemistry
Volume263
Issue number12
StatePublished - 1988
Externally publishedYes

Fingerprint

Lipid A
Lipopolysaccharides
Rhodobacter sphaeroides
Fatty Acids
Silicic Acid
Column chromatography
Disaccharides
Glucosamine
Structural analysis
Mass spectrometry
Toxicity
Chromatography
Desorption
Mass Spectrometry
Lasers
Liquids
monophosphoryl lipid A

ASJC Scopus subject areas

  • Biochemistry

Cite this

Location of fatty acids in lipid A obtained from lipopolysaccharide of Rhodopseudomons sphaeroides ATCC 17023. / Qureshi, N.; Honovich, J. P.; Hara, H.; Cotter, Robert J.; Takayama, K.

In: Journal of Biological Chemistry, Vol. 263, No. 12, 1988, p. 5502-5504.

Research output: Contribution to journalArticle

@article{69f2d1ec3d964e71a356eaf84bcb7505,
title = "Location of fatty acids in lipid A obtained from lipopolysaccharide of Rhodopseudomons sphaeroides ATCC 17023",
abstract = "Monophosphoryl lipid A (MLA) obtained from the lipopolysaccharide of Rhodopseudomonas sphaeroides ATCC 17023 was initially purified by silicic acid column chromatography to yield a single major pentaacyl MLA fraction. This fraction was methylated and further purified by reverse-phase high performance liquid chromtography to yield three prominent peak fractions. Laser desorption mass spectrometry of these three fractions allowed us to complete the important structural analysis of lipid A from this source. Three structurally distinct forms of dimethyl MLAwere identified where M(r) = 1447, 1449, and 1451 atomic mass units. These forms differed only by the presence or absence of unsaturation and keto group in the fatty acids. We established that the acyloxyacyl group (either Δ7-tetradecenoyloxytetradecanoate or tetradecanoyloxytetradecanoate) and the 3-ketotetradecanoate or hydroxytertadecanoate occupied the 2'- and 2-positions of the glucosamine disaccharide, respectively. Analysis of several minor fractions suggests that there is considerable structural heterogeneity in the MLA. With this new knowledge, the study of the structure-to-function relationship of the reported lack of toxicity of lipopolysaccharide from R. sphaeroides can be completed.",
author = "N. Qureshi and Honovich, {J. P.} and H. Hara and Cotter, {Robert J.} and K. Takayama",
year = "1988",
language = "English (US)",
volume = "263",
pages = "5502--5504",
journal = "Journal of Biological Chemistry",
issn = "0021-9258",
publisher = "American Society for Biochemistry and Molecular Biology Inc.",
number = "12",

}

TY - JOUR

T1 - Location of fatty acids in lipid A obtained from lipopolysaccharide of Rhodopseudomons sphaeroides ATCC 17023

AU - Qureshi, N.

AU - Honovich, J. P.

AU - Hara, H.

AU - Cotter, Robert J.

AU - Takayama, K.

PY - 1988

Y1 - 1988

N2 - Monophosphoryl lipid A (MLA) obtained from the lipopolysaccharide of Rhodopseudomonas sphaeroides ATCC 17023 was initially purified by silicic acid column chromatography to yield a single major pentaacyl MLA fraction. This fraction was methylated and further purified by reverse-phase high performance liquid chromtography to yield three prominent peak fractions. Laser desorption mass spectrometry of these three fractions allowed us to complete the important structural analysis of lipid A from this source. Three structurally distinct forms of dimethyl MLAwere identified where M(r) = 1447, 1449, and 1451 atomic mass units. These forms differed only by the presence or absence of unsaturation and keto group in the fatty acids. We established that the acyloxyacyl group (either Δ7-tetradecenoyloxytetradecanoate or tetradecanoyloxytetradecanoate) and the 3-ketotetradecanoate or hydroxytertadecanoate occupied the 2'- and 2-positions of the glucosamine disaccharide, respectively. Analysis of several minor fractions suggests that there is considerable structural heterogeneity in the MLA. With this new knowledge, the study of the structure-to-function relationship of the reported lack of toxicity of lipopolysaccharide from R. sphaeroides can be completed.

AB - Monophosphoryl lipid A (MLA) obtained from the lipopolysaccharide of Rhodopseudomonas sphaeroides ATCC 17023 was initially purified by silicic acid column chromatography to yield a single major pentaacyl MLA fraction. This fraction was methylated and further purified by reverse-phase high performance liquid chromtography to yield three prominent peak fractions. Laser desorption mass spectrometry of these three fractions allowed us to complete the important structural analysis of lipid A from this source. Three structurally distinct forms of dimethyl MLAwere identified where M(r) = 1447, 1449, and 1451 atomic mass units. These forms differed only by the presence or absence of unsaturation and keto group in the fatty acids. We established that the acyloxyacyl group (either Δ7-tetradecenoyloxytetradecanoate or tetradecanoyloxytetradecanoate) and the 3-ketotetradecanoate or hydroxytertadecanoate occupied the 2'- and 2-positions of the glucosamine disaccharide, respectively. Analysis of several minor fractions suggests that there is considerable structural heterogeneity in the MLA. With this new knowledge, the study of the structure-to-function relationship of the reported lack of toxicity of lipopolysaccharide from R. sphaeroides can be completed.

UR - http://www.scopus.com/inward/record.url?scp=0023901618&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023901618&partnerID=8YFLogxK

M3 - Article

C2 - 3258599

AN - SCOPUS:0023901618

VL - 263

SP - 5502

EP - 5504

JO - Journal of Biological Chemistry

JF - Journal of Biological Chemistry

SN - 0021-9258

IS - 12

ER -