Fermentation of long chain compounds byTorulopsis magnoliaeIII. Preparation of dicarboxylic acids from hydroxy fatty acid sophorosides

1966 ◽  
Vol 43 (3) ◽  
pp. 153-156 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer
Keyword(s):  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Dicarboxylic Acids ◽  
Chain Compounds ◽  
Long Chain

Fermentation of long-chain compounds by Torulopsis apicola. IV. Products from esters and hydrocarbons with 14 and 15 carbon atoms and from methyl palmitoleate

1968 ◽  
Vol 46 (9) ◽  
pp. 1523-1528 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Carbon Chain ◽  
Hydroxy Fatty Acids ◽  
Hexadecenoic Acid ◽  
Hydroxy Acids ◽  
Chain Compounds ◽  
Long Chain ◽  
Direct Hydroxylation

Esters and hydrocarbons, containing 14 and 15 carbon atoms, are converted to the hydroxy fatty acid portions of glycosides by Torulopsis apicola in yields of 10–20%. When C-15 compounds are fermented, almost half of the hydroxy acids which are produced are 16-hydroxy C-17 acids. The carbon chain of the substrate is first lengthened by two carbon atoms and then hydroxylated. Direct hydroxylation also occurs, to a lesser extent, giving both 14-hydroxy- and 15-hydroxypentadecanoic acids. Similar results are obtained when C-14 compounds are used. Lengthening of the chain followed by hydroxylation gives rise to hydroxy C-16 acids and direct hydroxylation produces 13-hydroxy- and 14-hydroxytetradecanoic acids. Primary and secondary C-14 and C-15 alcohols were also isolated from the products of hydrocarbon fermentation (2.5–5 % yield). Methyl palmitoleate is converted to hydroxy fatty acids in yields of 40–70%, the major component of which is 16-hydroxy-cis-9-hexadecenoic acid.

THE FERMENTATION OF LONG-CHAIN COMPOUNDS BY TORULOPSIS MAGNOLIAE: I. STRUCTURES OF THE HYDROXY FATTY ACIDS OBTAINED BY THE FERMENTATION OF FATTY ACIDS AND HYDROCARBONS

1962 ◽  
Vol 40 (7) ◽  
pp. 1326-1338 ◽  
Author(s):  
A. P. Tulloch ◽  
J. F. T. Spencer ◽  
P. A. J. Gorin
Keyword(s):  
Fatty Acids ◽  
Carbon Atom ◽  
Chain Length ◽  
Hydroxy Fatty Acid ◽  
Hydroxyl Group ◽  
Fatty Esters ◽  
Degree Of Unsaturation ◽  
Chain Compounds ◽  
Chain Lengths ◽  
Long Chain

The yield of extracellular glycolipid produced by Torulopsis magnoliae is increased three-to five-fold by the addition of suitable compounds to the growing culture. The supplement, which can be a long-chain acid, ester, hydrocarbon, or glyceride, is hydroxylated and converted to hydroxy fatty acid sophorosides. Fatty esters of all chain lengths from C16 to C22, including several unsaturated esters, and even-numbered hydrocarbons from C16 to C24 are readily fermented. Shorter-chain compounds are used poorly or not at all. With compounds of 16 to 18 carbon atoms, hydroxylation occurs at the terminal or penultimate carbon atom, depending on degree of unsaturation and chain length. Substrates of more than 18 carbon atoms are mainly reduced in chain length by one or more two-carbon units and hydroxylated, giving C17 or C18 acids with the hydroxyl group on the penultimate carbon atom. The various enzymic reactions which occur during the fermentation are discussed.

scholarly journals A Biocatalytic Cascade Reaction to Access a Valuable Long‐Chain ω‐Hydroxy Fatty Acid

ChemCatChem ◽  
2020 ◽  
Vol 12 (16) ◽  
pp. 4084-4089
Author(s):  
Aileen Becker ◽  
Dominique Böttcher ◽  
Werner Katzer ◽  
Karsten Siems ◽  
Lutz Müller‐Kuhrt ◽  
...  
Keyword(s):  
Fatty Acid ◽  
Hydroxy Fatty Acid ◽  
Cascade Reaction ◽  
Long Chain

scholarly journals A new series of long-chain dicarboxylic acids with vicinal dimethyl branching found as major components of the lipids of Butyrivibrio spp

1979 ◽  
Vol 183 (3) ◽  
pp. 691-700 ◽  
Author(s):  
R A Klein ◽  
G P Hazlewood ◽  
P Kemp ◽  
R M C Dawson
Keyword(s):  
Molecular Weight ◽  
Fatty Acid ◽  
High Molecular Weight ◽  
Mass Spectroscopy ◽  
Major Part ◽  
Dicarboxylic Acids ◽  
Synthetic Compounds ◽  
High Molecular Weight Component ◽  
Complex Lipids ◽  
Long Chain

1. Some members of the genus Butyrivibrio, including a general fatty acid auxotroph (strain S2), contain as a major part of their complex lipids a high-molecular-weight component that is probably formed by the union of two fatty acid chains [Hazlewood & Dawson (1979) J. Gen. Microbiol. 112, 15–27]. 2. Proton and 13C n.m.r. and i.r. and mass spectroscopy were used to examine a homologous series of these moieties and, in addition, the hydrocarbon derivative of one homologue and several synthetic compounds. 3. The results indicate that the high-molecular-weight components are a series of long-chain dicarboxylic acids containing vicinal dimethyl branching, located near the centre of the chain.

The effects of low-ratio n-6/n-3 PUFA on biomarkers of inflammation: a systematic review and meta-analysis

2021 ◽  
Author(s):  
Yali Wei ◽  
Yan Meng ◽  
Na Li ◽  
Qian Wang ◽  
Liyong Chen
Keyword(s):  
Systematic Review ◽  
Fatty Acid ◽  
Polyunsaturated Fatty Acid ◽  
Meta Analysis ◽  
Chain Polyunsaturated Fatty Acid ◽  
Inflammation Markers ◽  
Pufa Supplementation ◽  
Long Chain

The purpose of the systematic review and meta-analysis was to determine if low-ratio n-6/n-3 long-chain polyunsaturated fatty acid (PUFA) supplementation affects serum inflammation markers based on current studies.

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