Conformation and packing properties of phosphatidic acid: The crystal structure of monosodium dimyristoylphosphatidate

Harlos, K.; Eibl, H.; Pascher, I.; Sundell, Staffan

doi:10.1016/0009-3084(84)90037-9

Cited by 82 publications

(51 citation statements)

References 25 publications

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“…This is due to the strong intermolecular hydrogen bonds [9], formed in PA between phosphate groups. These interactions between --PO groups, that are the most likely candidate for water binding in phospholipids (PL) [11], could prevent high PA hydration, as suggested for other hydrogen bonded molecules [31]. In contrast, PC molecules are bonded together through water molecules [31].…”

Section: Discussionmentioning

confidence: 98%

“…The small cross-section of the phosphate group cannot tightly cover the layer surface [9], so that water molecules have to be accommodated as spacer molecules into the polar headgroup region [11]. It was suggested that, in a biological membrane, PA forms hydrogen bonded dimers [30] or strands [11].…”

Section: Discussionmentioning

confidence: 99%

“…PA, normally a minor component of cellular plasmamembranes [6], is rapidly accumulated following the activation of the phospha-tidylinositol cycle by a variety of functional stimuli [7,8], some of which involve fusional processes. PA has a characteristic configuration in the bilayer phase since its phosphatidic group packs with small cross section relative to the hydrocarbon chains; in pure PA liposomes and in mixtures, specific structural organization of PA occurs, in the range of physiological pH [9], probably through the formation of hydrogen bonds which link PA phosphate groups [10,11]. This behaviour modifies water organization at the membrane surface [9] and thermotropic properties of the membrane [12].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Phosphatidic acid affects structural organization of phosphatidylcholine liposomes. A study of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl,1,3,5-hexatriene (TMA-DPH) fluorescence decay using distributional analysis

Zolese

Gratton

Curatola

1990

Chemistry and Physics of Lipids

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Section: Discussionmentioning

confidence: 98%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Phosphatidic acid affects structural organization of phosphatidylcholine liposomes. A study of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl,1,3,5-hexatriene (TMA-DPH) fluorescence decay using distributional analysis

Zolese

Gratton

Curatola

1990

Chemistry and Physics of Lipids

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“…It is possible that there is a reorientation of the polar head group in such a tightly packed film inducing a new organization of the hydrogen-bond network which is less efficient for proton transfer. X-ray studies have shown that although the conformation of the polar group was different from other lipids (no direct contact between phosphate groups), intercalated water molecules do play a decisive role in the stability of the system [27].…”

Section: Discussionmentioning

confidence: 99%

Lateral proton conduction at a lipid/water interface. Effect of lipid nature and ionic content of the aqueous phase

1987

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Fast lateral proton conduction was observed along the lipidiwater interface using a fluorescence technique. This conduction can be detected for a large number of lipids, both phospholipids and glycolipids. The efficiency of the proton transfer is dependent on the molecular packing of the host lipid at a given surface pressure. The proton conduction which is present in the liquid expanded state is abolished by the transition to the liquid condensed state. The proton transfer is affected slightly by the ionic content of the aqueous subphase except in the case of calcium which can inhibit the conduction along phosphatidylglyceroethanolamine.We suggest that the transfer of the protons occurs along a bidimensional hydrogen-bond network formed from the polar head groups, their water molecules of hydration and the water molecules which are intercalated between the lipid molecules.One of the basic requirements for the occurrence of a 'localized' mechanism of energy transduction [l -41 is the existence of a proton pathway along the membrane. Using a fluorescence method with lipid monolayers spread at the air/ water interface, we were able to detect such a proton pathway along the polar heads of phosphatidylethanolamine [5, 61. This technique provided experimental evidence that protons moved 20 times faster along the polar heads ('localized pathways') than in the bulk aqueous phase ('delocalized pathways'). This process occurs as long as the monolayer is structured, i.e. that its surface potential is different from zero. The time required by protons to move from one position to another was not affected by the packing of the film, although the number of protons-apparently transferred was strongly controlled by this, structural parameter. A systematic investigation of the physical parameters modulating this process showed that it depended on a bidimensional diffusion of protons along or within the polar heads.Using a laser-pulse-induced pH jump, Gutman and coworkers were able to demonstrate that surface groups on a high-molecular-mass body, such as neutral red bound to a detergent micelle, exchange protons at a very fast rate [7, 81. This observation was tentatively explained by the close proximity of the reactants and by the two-dimensional nature of the system 191. More recently, this approach was extended Correspondence to J.

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“…The torsion angles around the glycerol ester part of the molecule as described by the notation of Sundaralingam (18) are compared to other pertinent lipids in Table 4. The conformation of glycerol backbone (0 angles) is quite similar to the A conformer of 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) (14,15) but different from phosphatidylethanolamine (14,19), tricaprin (20), 1,2-diacyl-snglycerols (12,13), dimyristoyl glycerol phosphate (DMPA) (21), and dilauroyl phosphatidyl-N,N-dimethylethanolamine Abbreviations: PP2, 1,2-dipahnitoyl-3-acetyl-sn-glycerol; DMPC, 1,2-dimyristoyl-sn-glycero-3-phosphocholine; DMPA, dimyristoyl glycerol phosphate; DPG, 1,2-dipalmitoyl-sn-glycerol.…”

mentioning

confidence: 99%

Single crystal structure of a mixed-chain triacylglycerol: 1,2-dipalmitoyl-3-acetyl-sn-glycerol.

Goto¹,

Kodali²,

Small³

et al. 1992

Proc. Natl. Acad. Sci. U.S.A.

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The mixed chain triacylglycerol 1,2-dipalmitoyl-3-acetyl-sn-glycerol was synthesized and its crystal structure was determined to a rinal reliability factor (R) of 0.11. Two molecules are present in the monoclinic unit cell: space group P21; a = 5.375(1), b = 8.286(2), c = 42.96(1) i; 13 = 93.30(2)°, V = 1910 A3, p = 1.065 g/cm3, and jt = 5.7 cm-'. The structure is a trilayer: a bilayer of palmitate chains packed in the (3 mode (T//) and an interdigitated monolayer of acetates. The glycerol backbone and acetate extend roughly linearly from the sn-i chain. The sn-2 chain bends around the C-2 carbon to lie next to the sn-i chain. Analysis of the torsion angles indicate that the glycerol conformation of 1,2-dipalmitoyl-3-acetyl-sn-glycerol is markedly different from single acid triacylglycerols and from 1,2-diacyl-sn-glycerols but very similar to 1,2-dimyristoyl-sn-glycero-3-phosphocholine.Acylglycerols are ubiquitous and highly prevalent biological molecules. Triacylglycerols are the major form of lipids stored in tissues of both plants and animals. Although their physical properties such as polymorphic forms, melting and transition temperatures, volumes, and viscosity are generally known (1-3), specific detailed crystal structures are largely lacking. Only two structures on single-chain triacylglycerols, tricaprin by Jensen and Mabis in 1963 (4) and trilaurin by Larsson in 1964 (5), have been published. A single complex triacylglyceride structure, 2-(11-bromoundecanoyl)-1,1'-dicaprin, was published (6), but its structure, especially the conformation of the glycerol and the chain orientation, are quite similar to the structure of single-chain triacylglycerols (4, 5). Our understanding of the structure and polymorphism of acylglycerols would be greatly enhanced by knowing the crystal structures of some of the forms of mixed-chain triacylglycerols. Diacylglycerols are intermediates in the metabolism of triacylglycerols and phospholipids. Diacylglycerols are also membrane-oriented (7) second messengers participating in signal transduction across membranes (8, 9). The biologically active form of diacylglycerols are the membrane-bound 1,2-diacyl-sn-glycerols (10). The general structure of saturated 1,2-diacyl-sn-glycerols has been reported (11) and the crystal structure of 1,2-dilauroyl-sn-glycerol (12) and 1,2-dipalmitoyl-sn-glycerol (13) have been solved. We have synthesized the three acetyl derivative of 1,2-dipalmitoyl-sn-glycerol and defined its crystal structure.$ The structure of this triacylglycerol with an acetate in position 3 differs considerably around the glycerol backbone from 1,2-diacylglycerols (12-14) or simple acid triacylglycerols such as trilaurin (4, 5). The glycerol conformation is, however, quite similar to one of the two conformers of dimyristoyl phosphatidylcholine (15). 11 MATERIALS AND METHODS 1,2-Dipalmitoyl-3-acetyl-sn-glycerol (PP2) was synthesized as described by Kodali et al. (16). After several trials of crystallization, a fairly good crystal with dimensions of 0.02 x 0.06 x 0.5 ...

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Conformation and packing properties of phosphatidic acid: The crystal structure of monosodium dimyristoylphosphatidate

Cited by 82 publications

References 25 publications

Phosphatidic acid affects structural organization of phosphatidylcholine liposomes. A study of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl,1,3,5-hexatriene (TMA-DPH) fluorescence decay using distributional analysis

Phosphatidic acid affects structural organization of phosphatidylcholine liposomes. A study of 1,6-diphenyl-1,3,5-hexatriene (DPH) and 1-(4-trimethylammonium-phenyl)-6-phenyl,1,3,5-hexatriene (TMA-DPH) fluorescence decay using distributional analysis

Lateral proton conduction at a lipid/water interface. Effect of lipid nature and ionic content of the aqueous phase

Single crystal structure of a mixed-chain triacylglycerol: 1,2-dipalmitoyl-3-acetyl-sn-glycerol.

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