Zur Stereochemie der vierfach konjugiert‐ungesättigten Parinarsäuren

Kaufmann, H. P.; Sud, R. K.

doi:10.1002/cber.19590921121

Cited by 19 publications

(8 citation statements)

References 20 publications

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“…A more classical approach involves consecutive Wittig and Wadsworth-Horner-Emmons reactions 219,220. Regardless of the synthetic approach, the final polyene must be isomerized to the all-( E ) isomer, typically by the use of iodine 217,224…”

Section: Fluorescent Analogs Of Phospholipids and Fatty Acidsmentioning

confidence: 99%

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

2010

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Section: Fluorescent Analogs Of Phospholipids and Fatty Acidsmentioning

confidence: 99%

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

2010

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“…By this method dimorphecolic acid (XIV) was shown to be a trans,trans diene (266), the dehydration product (XV) of ricinelaidic acid ("Mangold's acid") was also shown to be a trans,trans diene (24), and the configuration of the diene substituent in the pyrethrolones (XVI) was shown to be trans (132). Configurations have also been assigned to the triene systems in «-and /3-eleostearic acids (XVII) (24,100) and their isomer punicic acid (144), «-and /3-licanic acids (XVIII) (216), the isomers of the tetraene, parinaric acid (XIX) (184), alioand neoalloocimene (XX) (13,117), and a series of simple trienes (7) by the use of the Diels-Alder reaction. This method was also of great utility in elucidating the structure and stereochemistry of irradiation products of ergosterol (149).…”

Section: Ch3mentioning

confidence: 98%

Stereochemistry of the Diels-Alder Reaction.

Martin¹,

Hill²

1961

Chem. Rev.

317

110

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“…For general reviews of the occurrence and chemistry of fatty acids with conjugated unsaturation, see Hopkins (1972) and Solodovnik (1967). AND SIMONI (Kaufmann and Sud, 1959). We will refer to these isomers as cisand trans-PnA, respectively.…”

mentioning

confidence: 99%

Conjugated polyene fatty acids as fluorescent probes: synthetic phospholipid membrane studies

Sklar¹,

Hudson²,

Simoni³

1977

Biochemistry

328

183

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The preparation of polyene fatty acid membrane probes cis- and trans-parinaric acid and parinaroylphosphatidylcholines and their use in studies of several one- and two- component lipid systems are described. The fluorescence quantum yield of trans-parinaric acid in dipalmitoylphosphatidylcholine at 20 degrees C is approximately 0.3; the quantum yield in aqueous solution is negligibly small. Thermal-phase transitions in single-component phospholipid dispersions are monitored with absorption and fluorescence excitation peak position, fluorescence intensity, lifetime, and polarization. The transition temperatures observed are consistent with previous determinations. Shifts in the absorption peak position are related to the bilayer expansion as it undergoes the gel to liquid-crystalline transition, while fluorescence depolarization provides semiquantitative information concerning molecular motion of the probe in the bilayer. A long fluorescence lifetime component is observed for parinaric acid in the solid phase (up to 50 ns), and a short lifetime component is observed (ca. 5 ns) in the fluid phase of dipalmitoylphosphatidylcholine; both lifetime components are observed in the transition region. In most phospholipids, cis-parinaric acid detects the melting transition at about 1 degree C lower than trans-parinaric acid. Partitioning experiments involving mixed populations of phospholipid vesicles show that trans-parinaric acid preferentially associates with solid-phase lipids, while cis-parinaric acid shows a more equal distribution between solid and fluid lipids. The binding of cis-parinaric acid to dipalmitoylphosphatidylcholine at 25 degrees C is described as partitioning of parinaric acid between lipid vesicles and the aqueous phase with a partition coefficient of 5 X 10(5). Several rates are observed in the binding process which are interpreted as rapid outer monolayer uptake and a much slower process of interlamellar exchange. The phase diagram of the binary lipid mixture dipalmitoylphosphatidylcholine-dipalmitoylphosphatidylethanolamine has also been examined and found to be essentially identical to the one constructed using a nitroxide probe.

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Zur Stereochemie der vierfach konjugiert‐ungesättigten Parinarsäuren

Cited by 19 publications

References 20 publications

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

Fluorescent Analogs of Biomolecular Building Blocks: Design, Properties, and Applications

Stereochemistry of the Diels-Alder Reaction.

Conjugated polyene fatty acids as fluorescent probes: synthetic phospholipid membrane studies

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