A convenient synthesis of phosphatidylcholines: acylation of sn-glycero-3-phosphocholine with fatty acid anhydride and 4-pyrrolidinopyridine.

Patel, Kanu; Morrisett, Joel D.; Sparrow, James T.

doi:10.1016/s0022-2275(20)40592-9

Cited by 109 publications

(23 citation statements)

References 18 publications

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“…Synthesis and Purification of Phosphatidylcholines. The PC's were synthesized by the method of Patel et al (1979). The crude reaction product from 4 mmol of starting fatty acid was diluted to 35 cm3 with chloroform and applied directly to a 15-g column of silicic acid packed in chloroform.…”

Section: Methodsmentioning

confidence: 60%

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Thermotropic phase behavior of model membranes composed of phosphatidylcholines containing methyl iso-branched fatty acids. 1. Differential scanning calorimetric studies

Lewis¹,

McElhaney²

1985

Biochemistry

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The thermotropic phase behavior of aqueous dispersions of phosphatidylcholines containing one of a series of methyl iso-branched fatty acyl chains was studied by differential scanning calorimetry. These compounds exhibit a complex phase behavior on heating which includes two endothermic events, a gel/gel transition, involving a molecular packing rearrangement between two gel-state forms, and a gel/liquid-crystalline phase transition, involving the melting of the hydrocarbon chains. The gel to liquid-crystalline transition is a relatively fast, highly cooperative process which exhibits a lower transition temperature and enthalpy than do the chain-melting transitions of saturated straight-chain phosphatidylcholines of similar acyl chain length. In addition, the gel to liquid-crystalline phase transition temperature is relatively insensitive to the composition of the aqueous phase. In contrast, the gel/gel transition is a slow process of lower cooperativity than the gel/liquid-crystalline phase transition and is sensitive to the composition of the bulk aqueous phase. The gel/gel transitions of the methyl iso-branched phosphatidylcholines have very different thermodynamic properties and depend in a different way on hydrocarbon chain length than do either the "subtransitions" or the "pretransitions" observed with linear saturated phosphatidylcholines. The gel/gel and gel/liquid-crystalline transitions are apparently concomitant for the shorter chain iso-branched phosphatidylcholines but diverge on the temperature scale with increasing chain length, with a pronounced odd/even alternation of the characteristic temperatures of the gel/gel transition.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Methodsmentioning

confidence: 60%

“…The acylation of the L-a-glycerophosphocholine proceeded in yields comparable to those described by Patel et al (1979).…”

Section: Methodsmentioning

confidence: 99%

Thermotropic phase behavior of model membranes composed of phosphatidylcholines containing methyl iso-branched fatty acids. 1. Differential scanning calorimetric studies

Lewis¹,

McElhaney²

1985

Biochemistry

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“…The phosphatidylcholines used in this study were synthesized from commercially available highly purified fatty acids (Nu-Chek Prep Inc.) using the acylation procedure of Patel et al (1979). The lipids were subsequently purified by methods known to produce highly pure samples [see Lewis and McElhaney (1985a)], lyophilized from benzene, and stored under nitrogen at -20 °C.…”

Section: Methodsmentioning

confidence: 99%

Thermotropic phase behavior of model membranes composed of phosphatidylcholines containing cis-monounsaturated acyl chain homologs of oleic acid: differential scanning calorimetric and phosphorus-31 NMR spectroscopic studies

Lewis¹,

Sykes²,

McElhaney³

1988

Biochemistry

126

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The thermotropic phase behavior of dioleoylphosphatidylcholine and six of its longer chain homologues was studied by differential scanning calorimetry and 31P nuclear magnetic resonance (NMR) spectroscopy. Aqueous dispersions of these compounds all exhibit a single endotherm upon heating but upon cooling exhibit at least two exotherms, both of which occur at temperatures lower than those of their heating endotherm. The single transition observed upon heating was shown by 31P NMR spectroscopy to be a net conversion from a condensed, subgel-like phase (Lc phase) to the liquid-crystalline state. Aqueous ethylene glycol dispersions of these compounds also exhibit single endotherms upon heating and cooling exotherms centered at temperatures lower than those of their corresponding heating endotherm. However, the behavior of the aqueous ethylene glycol dispersions differs with respect to their transition temperatures and enthalpies as well as the extent of "undercooling" observed, and there is some evidence of discontinuities in the cooling behavior of the odd- and even-numbered members of the homologous series. Like the aqueous dispersions, 31P NMR spectroscopy also shows that the calorimetric events observed in aqueous ethylene glycol involve net interconversions between an Lc-like phase and the liquid-crystalline state. However, the Lc phase formed in aqueous ethylene glycol dispersions exhibits a considerably broader powder pattern than that observed in water. This, together with the fact that the transition enthalpies of the aqueous ethylene glycol dispersions are considerably higher than those of the aqueous dispersions, indicates that these lipids form more ordered Lc phases in aqueous ethylene glycol.(ABSTRACT TRUNCATED AT 250 WORDS)

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“…were prepared in HPLC-grade, argon-bubbled chloroform and were radiolabeled with [1-14C]DMPC to a level of 3.2 mmol of labeled lipid/mol of unlabeled lipid. [1-14C]DMPC was prepared by the method of Patel et al (1979) AL) according to the procedures of Dawson (1967). The commercial, chromatographically pure material was further purified by extraction with disodium ethylenediaminetetraacetate (Na2EDTA)' solution followed by precipitation from acetone (Lentz et al, 1980(Lentz et al, , 1982.…”

Section: Methodsmentioning

confidence: 99%

Transbilayer redistribution of phosphatidylglycerol in small, unilamellar vesicles induced by specific divalent cations

Lentz

Madden²,

Alford³

1982

Biochemistry

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A convenient synthesis of phosphatidylcholines: acylation of sn-glycero-3-phosphocholine with fatty acid anhydride and 4-pyrrolidinopyridine.

Cited by 109 publications

References 18 publications

Thermotropic phase behavior of model membranes composed of phosphatidylcholines containing methyl iso-branched fatty acids. 1. Differential scanning calorimetric studies

Thermotropic phase behavior of model membranes composed of phosphatidylcholines containing methyl iso-branched fatty acids. 1. Differential scanning calorimetric studies

Thermotropic phase behavior of model membranes composed of phosphatidylcholines containing cis-monounsaturated acyl chain homologs of oleic acid: differential scanning calorimetric and phosphorus-31 NMR spectroscopic studies

Transbilayer redistribution of phosphatidylglycerol in small, unilamellar vesicles induced by specific divalent cations

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