Chemistry and Biochemistry of Unsaturated Fatty Acids

Kunau, Wolf‐H.

doi:10.1002/anie.197600611

Cited by 34 publications

(10 citation statements)

References 194 publications

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“…The unsaturated sn-2 acyl chain may have [16][17][18][19][20][21][22] carbons; in addition, it contains 1-6 cis-double bonds (∆-bonds). Interestingly, two or more ∆-bonds in the sn-2 acyl chains are always methylene-interrupted, indicating that two neighboring cis-double bonds are invariably separated from each other in the sn-2 acyl chain by a methylene unit (3). It should be pointed out that (i) methylene-interrupted cis-double bonds are the hallmark of membrane lipids originated from animal cells, and (ii) these structural elements are absent in other basic biological molecules such as protein, nucleic acid, and carbohydrate.…”

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confidence: 99%

Mixed‐chain phospholipids: Structures and chain‐melting behavior

Huang

2001

Lipids

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It has long been established that diacyl phospholipids isolated from animal cell membranes are predominantly of a mixed-chain variety, meaning that the sn-1 and sn-2 acyl chains are saturated and unsaturated acyl chains, respectively. In general, monoenoic and dienoic acids are found in the sn-2 acyl chain of phosphatidylcholine (PtdCho), whereas polyenoic acids are in phosphatidylethanolamine (PtdEth). These unsaturated chains contain only cis-double bonds, which are always methylene-interrupted. In recent years, the structures and the chain-melting behavior of mixed-chain PtdCho and PtdEth have been systematically studied in this laboratory. Specifically, we have examined the effects of chain unsaturation of the sn-2 acyl chain on the phase transition temperature (Tm) of many PtdCho and PtdEth by high-resolution differential scanning calorimetry (DSC). The Tm values, for instance, obtained from all-unsaturated mixed-chain PtdEth derived from a common precursor can be grouped together according to their chemical formula to form a Tm-diagram. Hence, all the Tm values can be compared simply, systematically, and simultaneously using the Tm-diagram. In addition, the energy-minimized structures of mixed-chain phospholipids containing different numbers/positions of methylene-interrupted cis-double bonds have been simulated by molecular mechanics calculations (MM). In this review, the results of our MM and DSC studies carried out with various mixed-chain phospholipids are summarized. In addition, we emphasize that the combined approach of MM and DSC yields unique information that can correlate the various Tm-profiles seen in the Tm-diagram with the structural variation of mixed-chain lipids as caused by the introduction of different numbers/positions of methylene-interrupted cis-double bonds.

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confidence: 99%

Mixed‐chain phospholipids: Structures and chain‐melting behavior

Huang

2001

Lipids

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“…The metabolite is a L-isomer, for Lemieux and Giguere a ) described that D-3-HOA gave a specific rotation of -21 0 in CHCI 3 • It is well known that a hydration product of trans-2alkenoyl-CoA in the oxidative degradation of fatty acids is L-3-hydroxyacyl-CoA. 4…”

Section: ) Metabolism Of Trans-2-octenoic Acid (2-mentioning

confidence: 99%

Fungal Metabolism oftrans-2-Octenoic Acid

Tahara

Suzuki

Mizutani

1977

Agricultural and Biological Chemistry

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The metabolisms of trans-2-octenoic acid (2-0EA) and related compounds were investigated by using one of Mucor species which could reduce sorbic acid to trans-4-hexenol. In a phosphate buffer solution, 3-hydroxyoctanoic acid (3-HOA), monooctyl phosphate (OLP), I-octanol and I,3-octanediol were produced as metabolites of 2-0EA. It was elucidated that the conversion of 2-0EA into 3-HOA was reversible and finally most of the substrate was transformed into OLP via the following pathway: 3-HOA~2-0EA-.trans-2-octenol->l octanol-.OLP. Similarly, trans-3-octenol and mono-trans-3-octenyl phosphate were produced by the fungus as major metabolites of trans-3-octenoic acid.

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“…It is well known that a hydration product of trans-2-alkenoyl-CoA in the oxidative degradation of fatty acids is L-3-hydroxyacyl-CoA. 4) The time-course changes of metabolites of 2-OEA were examined over 33 hr to ascertain the interrelationships among metabolic inter- Reaction mixture: Wet cells 1 g/100 ml m/15 phosphate buffer (pH 6.0), glucose 5 % and substrates 4 mm (carboxylic acids were added as potassium salts). The reaction was carried out at 25°C for 6 hr on standing.…”

Section: ) Metabolism Of Trans-2-octenoic Acid (2-mentioning

confidence: 99%