Stereospecific Conversion of Oleic Acid to 10-Hydroxystearic Acid

Schroepfer, George J.

doi:10.1016/s0021-9258(18)96449-5

Cited by 62 publications

(3 citation statements)

References 14 publications

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“…Even if oleic acid is not used well by the Fak system in a mprF2 deletion background, we would expect to see it accumulate free in the membrane, and that would be reflected in our GC-FAME analysis. Another possibility is that there is increased oleate hydratase activity in the gene deletion background, which would result in accumulation of C 18:0 , which could then enter fatty acid elongation cycle, generating C 20:0 (Schroepfer, 1966;Niehaus et al, 1970;Kishino et al, 2013;Radka et al, 2021). We do note an accumulation of C 20:0 in this strain, but also in other strains, upon supplementation with oleic acid (Supplementary Table 4).…”

Section: Discussionmentioning

confidence: 75%

Enterococcus faecalis Readily Adapts Membrane Phospholipid Composition to Environmental and Genetic Perturbation

et al. 2021

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The bacterial lipid membrane, consisting both of fatty acid (acyl) tails and polar head groups, responds to changing conditions through alteration of either the acyl tails and/or head groups. This plasticity is critical for cell survival as it allows maintenance of both the protective nature of the membrane as well as functioning membrane protein complexes. Bacteria that live in fatty-acid rich environments, such as those found in the human host, can exploit host fatty acids to synthesize their own membranes, in turn, altering their physiology. Enterococcus faecalis is such an organism: it is a commensal of the mammalian intestine where it is exposed to fatty-acid rich bile, as well as a major cause of hospital infections during which it is exposed to fatty acid containing-serum. Within, we employed an untargeted approach to detect the most common phospholipid species of E. faecalis OG1RF via ultra-high performance liquid chromatography high-resolution mass spectrometry (UHPLC-HRMS). We examined not only how the composition responds upon exposure to host fatty acids but also how deletion of genes predicted to synthesize major polar head groups impact lipid composition. Regardless of genetic background and differing basal lipid composition, all strains were able to alter their lipid composition upon exposure to individual host fatty acids. Specific gene deletion strains, however, had altered survival to membrane damaging agents. Combined, the enterococcal lipidome is highly resilient in response to both genetic and environmental perturbation, likely contributing to stress survival.

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Section: Discussionmentioning

confidence: 75%

Enterococcus faecalis Readily Adapts Membrane Phospholipid Composition to Environmental and Genetic Perturbation

et al. 2021

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“…acid hydration observed in a pseudomonad (Niehaus et a!., 1970;Schroepfer, 1966) or by a direct hydroxylation mechanism. In order to distinguish between these two possibilities [10-14C]palmitoleic acid (cis-A9) was fed to V. faba leaf disks.…”

Section: Resultsmentioning

confidence: 99%

Structure and biosynthesis of the hydroxy fatty acids of cutin in Vicia faba leaves

Kolattukudy¹,

Walton²

1972

Biochemistry

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Cutin, the lipid polymer, which is the structural component of cuticle, was isolated from Vicia faba leaves by a combination of enzymatic and chemical techniques. Exhaustive hydrogenolysis of powdered cutin followed by thinlayer chromatography and a combination of gas chromatography and mass spectrometry showed that this cutin was composed of 10,16-dihydroxypalmitic acid (77.8 %), 9,16dihydroxypalmitic acid (7.

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“…To obtain more information on the location of a putative hydroxy substituent of the natural agent, N -BOC- 3 was reduced with CeCl 3 −NaBH 4 in CH 3 OH, deprotected with 4 N HCl−EtOAc to provide 4 as a 3:1 mixture of diastereomers, and subjected to electrospray MS fragmentation analysis. The agent 4 , like sphingosine, generated a strong fragment at m/z 30 indicative of a secondary hydroxy substituent fragmenting as CHOH …”

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confidence: 99%

Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide): A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

1996

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The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Δ-sleep-inducing peptide and prostaglandin D2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of sleep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep−wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.

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Stereospecific Conversion of Oleic Acid to 10-Hydroxystearic Acid

Cited by 62 publications

References 14 publications

Enterococcus faecalis Readily Adapts Membrane Phospholipid Composition to Environmental and Genetic Perturbation

Enterococcus faecalis Readily Adapts Membrane Phospholipid Composition to Environmental and Genetic Perturbation

Structure and biosynthesis of the hydroxy fatty acids of cutin in Vicia faba leaves

Structure Determination of an Endogenous Sleep-Inducing Lipid, cis-9-Octadecenamide (Oleamide): A Synthetic Approach to the Chemical Analysis of Trace Quantities of a Natural Product

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