Synthesis of 1,2-dipalmitoyl--glycer-3-yl---inositol 1-phosphate.

Ward, Jacob; Young, R. C.

doi:10.1016/s0040-4039(00)82254-6

Cited by 37 publications

(11 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The conformation of the PtdIns head group in aprotic DMSOd 6 (Fig. 3E) has been deduced from NMR data previously (45)(46)(47). in lamellar bilayers (54,55).…”

Section: Head Group Conformation and Orientationmentioning

confidence: 95%

Biophysical Properties of Phosphtidylglucoside and Phosphatidylinositol: Specific Differences in Head Group Interaction

Greimel

2018

TIGG

View full text Add to dashboard Cite

The size of the polar head group plays a key role in lipid biophysics, influencing membrane organization, phase behavior, including transition (melting) temperature, as well as lipid-lipid interactions, such as the umbrella effect. In general, small head groups are associated with high transition temperatures and tighter head group packing compared to lipids with large head groups. The head groups of phosphatidylglucoside (PtdGlc) and phosphatidylinositol (PtdIns) are configurational isomers with both featuring a sixmembered ring and a similar number of hydroxy functions. Interestingly, their chemical stability and biophysical properties differ significantly, despite their high structural similarity, comparable chemical size and weight, and presumably analogous head group orientation relative to the plasma membrane normal. PtdIns is known to exhibit a low transition temperature, limited lipid-lipid head group interaction, a high degree of head group hydration and an intramolecular hydrogen-bond even under fully hydrated conditions. PtdGlc on the other hand exhibits a ~20 degree higher transition temperature, extensive lipid-lipid head group interactions, a low degree of head group hydration and no intramolecular hydrogen-bond. Consequently, head group size in terms of lipid biophysics, refers not only to the immediate chemical size, but also includes the primary hydration shell.

show abstract

“…The conformation of the PtdIns head group in aprotic DMSOd 6 (Fig. 3E) has been deduced from NMR data previously (45)(46)(47). in lamellar bilayers (54,55).…”

Section: Head Group Conformation and Orientationmentioning

confidence: 95%

Biophysical Properties of Phosphtidylglucoside and Phosphatidylinositol: Specific Differences in Head Group Interaction

Greimel

2018

TIGG

View full text Add to dashboard Cite

show abstract

“…To a solution of racemic 1 -0-(tertbutyldiphenylsilyl)-2,3:5,6-di-0-isopropylidene-/Myo-inositol (1.16 g, 2.33 mmol) (Ward & Young, 1988) and dry pyridine (0.28 mL, 3.46 mmol) in anhydrous dioxane (13 mL) was added (-)-camphanic acid chloride (0.73 g, 3.37 mmol), and the mixture was stirred at room temperature for 4 h. Further (-)-camphanic acid chloride (0.24 g, 1.12 mmol) and pyridine (0.09 mL, 1.15 mmol) were added, and the reaction mixture was stirred for 16 h. Diethyl ether (70 mL) was added, and the organic layer was extracted with aqueous sodium chloride (20 mL) and then water (20 mL). The dried organic phase was evaporated and the residue purified by column chromatography to yield a mixture of the diastereomers 1 and 2 (1.44 g, 91%).…”

Section: Methodsmentioning

confidence: 99%

Substrate stereospecificity of phosphatidylinositol-specific phospholipase C from Bacillus cereus examined using the resolved enantiomers of synthetic myo-inositol 1-(4-nitrophenyl phosphate)

Leigh

Volwerk²,

Griffith³

et al. 1992

Biochemistry

View full text Add to dashboard Cite

The substrate stereospecificity of phosphatidylinositol-specific phospholipase C from Bacillus cereus is examined using the resolved optical isomers of synthetic myo-inositol 1-(4-nitrophenyl phosphate), a chromogenic substrate for the phospholipase. The synthetic route employs mild acid-labile protecting groups and separation of the substituted myo-inositol enantiomers as the (-)-camphanyl ester diastereomers. Measurements of the initial rates of cleavage of the D and L enantiomers of the nitrophenyl substrate by phosphatidylinositol-specific phospholipase C from B. cereus show that this enzyme is essentially stereospecific for the D enantiomer. Under identical conditions, the rate of cleavage of the L isomer is less than 0.2% of that observed for the D isomer. The same is observed for the highly homologous enzyme from Bacillus thuringiensis. There is no measurable inhibition by the L enantiomer of the B. cereus enzyme acting on the D enantiomer, even when the molar ratio of L:D is 5, indicating that binding of the L enantiomer to the phospholipase is negligible. Thus, the enzyme active site is exquisitely sensitive to the stereochemistry of the myo-inositol group of the substrate.

show abstract

“…The 1-O-phosphate of inositol building block 11 was partially deprotected over night with triethylamine-MeCN. Condensation between the resulting inositol mono-cyanoethyl phosphate salt and excess diglyceride (19) was effected by mesitylenesulfonyl chloride and 3-nitro-1,2,4-triazole (22, generating MSNT in situ) 46 and required no protection of the 4-OH (Scheme 3). Protected phosphatidylinositol 23 may be unblocked to give the parent PI ( 1), but in order to produce PI-4-Ps the installation of a phosphate group on the 4-OH was required.…”

Section: Preparation Of Protected Pis and Deprotection Of Pi-4-p Prec...mentioning

confidence: 99%

Synthesis of unsaturated phosphatidylinositol 4-phosphates and the effects of substrate unsaturation on SopB phosphatase activity

et al. 2015

View full text Add to dashboard Cite

In this paper evidence is presented that the fatty acid component of an inositide substrate affects the kinetic parameters of the lipid phosphatase Salmonella Outer Protein B (SopB). A succinct route was used to prepare the naturally occurring enantiomer of phosphatidylinositol 4-phosphate (PI-4-P) with saturated, as well as singly, triply and quadruply unsaturated, fatty acid esters, in four stages: (1) The enantiomers of 2,3:5,6-O-dicyclohexylidene-myo-inositol were resolved by crystallisation of their di(acetylmandelate) diastereoisomers. (2) The resulting diol was phosphorylated regio-selectively exclusively on the 1-O using the new reagent tri(2-cyanoethyl)phosphite. (3) With the 4-OH still unprotected, the glyceride was coupled using phosphate tri-ester methodology. (4) A final phosphorylation of the 4-O, followed by global deprotection under basic then acidic conditions, provided PI-4-P bearing a range of sn-1-stearoyl, sn-2-stearoyl, -oleoyl, -γ-linolenoyl and arachidonoyl, glycerides. Enzymological studies showed that the introduction of cis-unsaturated bonds has a measurable influence on the activity (relative Vmax) of SopB. Mono-unsaturated PI-4-P exhibited a five-fold higher activity, with a two-fold higher KM, over the saturated substrate, when presented in DOPC vesicles. Poly-unsaturated PI-4-P showed little further change with respect to the singly unsaturated species. This result, coupled with our previous report that saturated PI-4-P has much higher stored curvature elastic stress than PI, supports the hypothesis that the activity of inositide phosphatase SopB has a physical role in vivo.

show abstract

Synthesis of 1,2-dipalmitoyl--glycer-3-yl---inositol 1-phosphate.

Cited by 37 publications

References 7 publications

Biophysical Properties of Phosphtidylglucoside and Phosphatidylinositol: Specific Differences in Head Group Interaction

Biophysical Properties of Phosphtidylglucoside and Phosphatidylinositol: Specific Differences in Head Group Interaction

Substrate stereospecificity of phosphatidylinositol-specific phospholipase C from Bacillus cereus examined using the resolved enantiomers of synthetic myo-inositol 1-(4-nitrophenyl phosphate)

Synthesis of unsaturated phosphatidylinositol 4-phosphates and the effects of substrate unsaturation on SopB phosphatase activity

Contact Info

Product

Resources

About