ChemInform Abstract: Synthesis of an Analogue of Biosynthetic Precursor Ia of Lipid A by an Improved Method: A Novel Antagonist Containing Four (S)-3-Hydroxy Fatty Acids.

ChemInform ◽  
2010 ◽  
Vol 27 (4) ◽  
pp. no-no
Author(s):  
K. FUKASE ◽  
W.-C. LIU ◽  
Y. SUDA ◽  
M. OIKAWA ◽  
A. WADA ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Lipid A ◽  
Hydroxy Fatty Acids ◽  
Improved Method ◽  
Biosynthetic Precursor

Synthesis of an analog of biosynthetic precursor Ia of lipid A by an improved method: a novel antagonist containing four (S)-3-hydroxy fatty acids

1995 ◽  
Vol 36 (41) ◽  
pp. 7455-7458 ◽  
Author(s):  
Koichi Fukase ◽  
Wen-Chi Liu ◽  
Yasuo Suda ◽  
Masato Oikawa ◽  
Akira Wada ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Lipid A ◽  
Hydroxy Fatty Acids ◽  
Improved Method ◽  
Biosynthetic Precursor

An improved extraction method of 3-oh fatty acids for environmental reconstruction

2020 ◽  
Author(s):  
Chanamon Panbut
Keyword(s):  
Fatty Acids ◽  
Acid Hydrolysis ◽  
Lipid A ◽  
Environmental Changes ◽  
Solid Phase ◽  
Lipid Extraction ◽  
Heating Time ◽  
Hydroxy Fatty Acids ◽  
Environmental Reconstruction ◽  
Total Lipid Extraction

<p>3-hydroxy or beta-hydroxy fatty acids produced by Gram-negative bacteria are a novel proxy for assessment of the environmental changes. These compounds composed of lipopolysaccharide (LPS) of Lipid A, a core polysaccharide region, and an O-antigen polysaccharide chain. The improved method for the 3-hydroxy fatty acids extraction was proposed in this study. The 12 soil samples collected from the eastern US border along the coastline from Maine to Florida were generally processed by acid hydrolysis, methylation, total lipid extraction, and solid-phase chromatography, respectively. Fatty acids eventually can be separated from the main part of LPS and combined with a methyl group. However, in the stage of acid hydrolysis, the temperature was decreased to 55 °C, and heating time was extended in order to prevent the broken of volatile compounds and diminish the relative abundance of 3-OH fatty acids. The higher abundance of interested 3-OH fatty acids for the environmental reconstruction can potentially be extracted by this improvement than the classical protocol. This research will be further compared in terms of cost, experimental time and completeness of data between these two methods.</p>

Studies towards lipid A: a synthetic strategy for the enantioselective preparation of 3-hydroxy fatty acids

2006 ◽  
Vol 17 (20) ◽  
pp. 2839-2841 ◽  
Author(s):  
Annalisa Guaragna ◽  
Mauro De Nisco ◽  
Silvana Pedatella ◽  
Giovanni Palumbo
Keyword(s):  
Fatty Acids ◽  
Lipid A ◽  
Hydroxy Fatty Acids ◽  
Synthetic Strategy

scholarly journals Variation, Modification and Engineering of Lipid A in Endotoxin of Gram-Negative Bacteria

2021 ◽  
Vol 22 (5) ◽  
pp. 2281
Author(s):  
Kazuyoshi Kawahara
Keyword(s):  
Fatty Acids ◽  
Lipid A ◽  
Hydroxy Fatty Acids ◽  
Hydroxyl Groups ◽  
Gram Negative Bacteria ◽  
Vaccine Adjuvants ◽  
Phagocytic Cells ◽  
Gram Negative ◽  
Electrostatic Charges ◽  
Lipid A Structure

Lipid A of Gram-negative bacteria is known to represent a central role for the immunological activity of endotoxin. Chemical structure and biosynthetic pathways as well as specific receptors on phagocytic cells had been clarified by the beginning of the 21st century. Although the lipid A of enterobacteria including Escherichia coli share a common structure, other Gram-negative bacteria belonging to various classes of the phylum Proteobacteria and other taxonomical groups show wide variety of lipid A structure with relatively decreased endotoxic activity compared to that of E. coli. The structural diversity is produced from the difference of chain length of 3-hydroxy fatty acids and non-hydroxy fatty acids linked to their hydroxyl groups. In some bacteria, glucosamine in the backbone is substituted by another amino sugar, or phosphate groups bound to the backbone are modified. The variation of structure is also introduced by the enzymes that can modify electrostatic charges or acylation profiles of lipid A during or after its synthesis. Furthermore, lipid A structure can be artificially modified or engineered by the disruption and introduction of biosynthetic genes especially those of acyltransferases. These technologies may produce novel vaccine adjuvants or antagonistic drugs derived from endotoxin in the future.

scholarly journals Straight and branched (ω-1)-hydroxylated very long chain fatty acids are components of Bradyrhizobium lipid A.

2011 ◽  
Vol 58 (1) ◽  
Author(s):  
Adam Choma ◽  
Iwona Komaniecka
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Lipid A ◽  
Hydroxy Fatty Acids ◽  
Methyl Groups ◽  
Long Chain Fatty Acids ◽  
Straight Chain ◽  
Whole Cell ◽  
Alkyl Chains ◽  
Long Chain

Lipopolysaccharides of seven Bradyrhizobium strains and three whole-cell fatty acid preparations from bacteria isolated from nodules of Sarothamnus scoparius (common broom) were studied for the presence of very long chain (ω-1)-hydroxy fatty acids. Several such fatty acids were identified. Among them, straight-chain as well as mono- and dimethyl branched acids with chains in the range from 26 to 34 carbon atoms were found. Pyrrolidides and 4,4-dimethyloxazoline derivatives were used to determine the branching position. Carbons at the (ω-10) and/or (ω-11) positions in alkyl chains were points of attachment of methyl groups. These data complete the structure of bradyrhizobial lipid A with important details. The obtained results can be applied in the chemotaxonomy of Bradyrhizobium.

scholarly journals The Evaluation of the Role of Beta-Hydroxy Fatty Acids on Chronic Inflammation and Insulin Resistance

2006 ◽  
Vol 2006 ◽  
pp. 1-6 ◽  
Author(s):  
A. S. Soydan ◽  
H. S. Dokmetas ◽  
M. Cetin ◽  
A. Koyuncu ◽  
E. Kaptanoglu ◽  
...  
Keyword(s):  
Insulin Resistance ◽  
Fatty Acids ◽  
Lipid A ◽  
Culture Media ◽  
Inflammatory Diseases ◽  
Venous Blood ◽  
Hydroxy Fatty Acids ◽  
Sterile Inflammation ◽  
Chronic Inflammatory Diseases

β-hydroxy fatty acids are a major component of lipid A moiety of lipopolysaccaride. We aimed to investigate the role of freeβ-hydroxy fatty acids on inflammation, as well as to evaluate their effects on cytokine release from human blood cells, and whether they exist in plasma of patients with chronic inflammatory diseases with/without insulin resistance. Peripheral venous blood was incubated withβ-hydroxy lauric andβ-hydroxy myristic acids (each 100 ng, 1μg, 10μg/mL) up to 24 hours. Cytokines were measured from culture media and plasma. Free fatty acids and biochemical parameters were also measured from patients' plasma. Onlyβ-hydroxy lauric acid significantly stimulated interleukin-6 production at 10μg/mL compared to control (533.9±218.1versus438.3±219.6pg/mL,P<.05). However, freeβ-hydroxy lauric and myristic acids were not found in patients' plasma. Therefore, freeβ-hydroxy lauric and myristic acids do not seem to have a role on sterile inflammation in chronic inflammatory diseases associated with insulin resistance.

scholarly journals Sensitive assay, based on hydroxy fatty acids from lipopolysaccharide lipid A, for Gram-negative bacteria in sediments.

1982 ◽  
Vol 44 (5) ◽  
pp. 1170-1177 ◽  
Author(s):  
J H Parker ◽  
G A Smith ◽  
H L Fredrickson ◽  
J R Vestal ◽  
D C White
Keyword(s):  
Fatty Acids ◽  
Lipid A ◽  
Hydroxy Fatty Acids ◽  
Gram Negative Bacteria ◽  
Sensitive Assay ◽  
Gram Negative

scholarly journals Acyl Chain Specificity of the Acyltransferases LpxA and LpxD and Substrate Availability Contribute to Lipid A Fatty Acid Heterogeneity in Porphyromonas gingivalis

2008 ◽  
Vol 190 (13) ◽  
pp. 4549-4558 ◽  
Author(s):  
Brian W. Bainbridge ◽  
Lisa Karimi-Naser ◽  
Robert Reife ◽  
Fleur Blethen ◽  
Robert K. Ernst ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Porphyromonas Gingivalis ◽  
Lipid A ◽  
Acyl Chain ◽  
Hydroxy Fatty Acids ◽  
Homologous Gene ◽  
Substrate Availability ◽  
E Coli ◽  
Acyl Chain Length

ABSTRACT Porphyromonas gingivalis lipid A is heterogeneous with regard to the number, type, and placement of fatty acids. Analysis of lipid A by matrix-assisted laser desorption ionization-time of flight mass spectrometry reveals clusters of peaks differing by 14 mass units indicative of an altered distribution of the fatty acids generating different lipid A structures. To examine whether the transfer of hydroxy fatty acids with different chain lengths could account for the clustering of lipid A structures, P. gingivalis lpxA (lpxAPg ) and lpxDPg were cloned and expressed in Escherichia coli strains in which the homologous gene was mutated. Lipid A from strains expressing either of the P. gingivalis transferases was found to contain 16-carbon hydroxy fatty acids in addition to the normal E. coli 14-carbon hydroxy fatty acids, demonstrating that these acyltransferases display a relaxed acyl chain length specificity. Both LpxA and LpxD, from either E. coli or P. gingivalis, were also able to incorporate odd-chain fatty acids into lipid A when grown in the presence of 1% propionic acid. This indicates that E. coli lipid A acyltransferases do not have an absolute specificity for 14-carbon hydroxy fatty acids but can transfer fatty acids differing by one carbon unit if the fatty acid substrates are available. We conclude that the relaxed specificity of the P. gingivalis lipid A acyltransferases and the substrate availability account for the lipid A structural clusters that differ by 14 mass units observed in P. gingivalis lipopolysaccharide preparations.

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