I. Mesyl Esters of Glycerol

Baer, Erich; Newcombe, Alan G.

doi:10.1139/v51-092

Cited by 9 publications

(4 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…DL-Dipalmitoyl-oc-glycerophosphoric acid was prepared by a method combining features of those described by Baer (1951) and Paulus & Kennedy (1960). DL-Dipalmitin (1.0 g.), prepared according to the procedure of Howe & Malkin (1951), was dissolved in dry pyridine (25 ml.)…”

Section: Vol 87 137mentioning

confidence: 99%

Biosynthesis of phosphatidylinositol in rat brain

Thompson¹,

Strickland²,

Rossiter³

1963

Biochemical Journal

View full text Add to dashboard Cite

Section: Vol 87 137mentioning

confidence: 99%

Biosynthesis of phosphatidylinositol in rat brain

Thompson¹,

Strickland²,

Rossiter³

1963

Biochemical Journal

View full text Add to dashboard Cite

“…The acid chlorides of fatty acids separately deuterated in the 2, 3, 6, 10, and 14 positions [made by Kolbe electrolysis ( N g u y h -D i n h -N g u y h , 1968)] were prepared with a thionyl chloride-dimethylformamide method and used to acylate 3-0-benzyl-sn-glycerol as described (Sowden & Fischer, 1941). The compound was debenzylated and phosphorylated to yield the corresponding phosphatidic acid (Baer, 1951). Coupling of phosphatidic acid to Ncarbobenzoxy-O-benzyl-L-serine using triisopropylsulfonyl chloride was accomplished according to Aneja et al (1970).…”

mentioning

confidence: 99%

Bilayers of phosphatidylserine: a deuterium and phosphorus nuclear magnetic resonance study

Browning¹,

Seelig²

1980

Biochemistry

167

146

View full text Add to dashboard Cite

The structure and motion of the phosphatidylserine molecule in bilayers have been studied with deuterium and phosphorus-3 1 nuclear magnetic resonance. The phase behavior and the thermodynamic properties of phosphatidylserine were further characterized by means of spin-label electron paramagnetic resonance and differential scanning calorimetry. 1.2-Dipalmitoyl-, 1,2-dimyristoyl-, and 1,2-dioleoyl-snglycero-3-phosphoserine were selectively deuterated in the fatty acyl chains, in the glycerol backbone, and in both the 2 and 3 segments of the serine moiety. The residual deuterium quadrupole couplings and the phosphorus-3 1 chemical shielding anisotropy of lipid-water mixtures a t pH 7.0 in the absence of divalent cations were measured as a function of temperature and provided quantitative data on segmental motions of the serine head group, the phosphate linkage, the glycerol backbone, and the hydrocarbon region. The N M R data of phosphatidylserine are compared with those previously obtained for phosphatidylcholine and phosphatidylethanolamine. Qualitative and quantitative agreement exists for the ordering of the fatty acyl chains of all these lipids. In particular, in all phospholipids, the sn-2 chain is bent at the C-2 segment. The bilayer thickness as calculated from the deuterium N M R data is similar to that of phosphatidylcholine. The deuterium magnetic resonance spectra of the C-3 deuPhosphatidylserine is an interesting lipid in biological membranes. Primarily, this phospholipid can bind calcium to its head group, resulting in a broadening and a shift to higher temperatures of the gel to liquid-crystalline phase transition in pure phosphatidylserine membranes (Jacobson & Papahadjopoulos, 1975). This could be important in biological systems because this property would allow for a relatively fast change in the lipid phase a t a constant temperature. Work on phosphatidylserine in model systems has been mainly concerned with macroscopic properties of natural brain phosphatidylserine, i.e., bilayer lamellar spacings as studied with X-ray diffraction, electron micrographs of lamellar structures, phase transition temperatures, electrophoretic mobilities, monolayer properties, and extensive studies on ion binding. More microscopic properties such as chain ordering or head group structure and motion have not been studied. Compared with the extensive literature for phosphatidylcholine and phosphatidylethanolamine, there is a lack of physical data on synthetic phosphatidylserines. This deficiency has probably been due to the difficulty of the phosphatidylserine synthesis and the more complicated purification techniques required. Phosphatidylserine is also much less stable than either phosphatidylcholine or phosphatidylethanolamine. This instability is especially noticeable with DPPS;' the high transition temperature of 53 "C forces one to measure at temperatures where From the terated glycerol backbone of 1,2-dipalmitoyl-and 1,2-dioleoyl-sn-glycero-3-phosphoserine are similar to those of 1.2-dipalmitoyl-sn-glycero-3-pho...

show abstract

“…Sundler and Akesson (29) have reported on the AgNOa-TLC separation of the molecular species of phosphatidylethanolamine as the N-acetyl-O-methyl derivatives, which yield resolutions comparable to those reported for the trifluoroacetamides. Methylation with diazomethane, however, is experimentally dangerous and may be accompanied by transmethylation (30) and diazomethanolysis (31). The trifluoroacetamides are sufficiently nonpolar not to require methylation for satisfactory chromatography.…”

Section: Agno3-tlc Of Trifluoroacetamides Of Phosphatidylethanolaminementioning

confidence: 99%

Resolution of molecular species of intact serine and ethanolamine phosphatides by argentation chromatography of their trifluoroacetamides

Yeung

Kuksis

Marai

et al. 1977

Lipids

View full text Add to dashboard Cite

An effective resolution of intact phosphatidylserines on the basis of unsaturation has been achieved by conventional argentation thin layer chromatography (TLC) following trifluoracetylaction. The trifluoroacetamides are prepared by treatment with trifluoroacetic anhydride or N-methyl-bis-trifluoroacetamide. The acetamides are resolved with chloroform-methanol-water (65:25:4, v/v/v) on Silica Gel G containing 20% silver nitrate. Subfractions with 0-6 double bonds per molecule were obtained for the phosphatidylserines of pig and ox brain, pig erythrocytes, rat liver, and rabbit skeletal muscle. The preparation of trifluoroacetamides is also advantageous for the silver ion fractionation of phosphatidylethanolamines. The method is applicable to metabolic studies of molecular species using radioactive precursors of neutral lipids, phosphorus, and nitrogenous bases.

show abstract

I. Mesyl Esters of Glycerol

Cited by 9 publications

References 9 publications

Biosynthesis of phosphatidylinositol in rat brain

Biosynthesis of phosphatidylinositol in rat brain

Bilayers of phosphatidylserine: a deuterium and phosphorus nuclear magnetic resonance study

Resolution of molecular species of intact serine and ethanolamine phosphatides by argentation chromatography of their trifluoroacetamides

Contact Info

Product

Resources

About