Synthesis of<sup>15</sup>Enriched Phospholipids by Transphosphatidylation

Akoka, Serge; Meir, C.; Tellier, Charles; Belaud, C.; Poignant, Serge

doi:10.1080/00397918508076815

Cited by 8 publications

(6 citation statements)

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“…Homodimer 3 - 3 was then synthesized using an improved procedure as outlined in Scheme . In brief, 4 was converted, enzymatically, to the corresponding ethanolamine, 5 . Subsequent condensation with di-3-thiobis[succinimidyl propionate] (DSP) afforded 3 - 3 .…”

Section: Results and Discussionmentioning

confidence: 99%

Push–Pull Mechanism for Lipid Raft Formation

et al. 2014

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A quantitative assessment has been made of the interaction between exchangeable mimics of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) and cholesterol in the liquid-ordered (l0) and the liquid-disordered (ld) states using the nearest-neighbor recognition (NNR) method. This assessment has established that these lipids mix ideally in the l0 phase (i.e., they show no net attraction or repulsion toward each other) but exhibit repulsive interactions in the ld phase. The implications of these findings for the interactions between unsaturated phospholipids and cholesterol in eukaryotic cell membranes are briefly discussed.

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Section: Results and Discussionmentioning

confidence: 99%

Push–Pull Mechanism for Lipid Raft Formation

et al. 2014

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“…The method described was adapted from that used by Akora et al for the preparation of methyl esters. 35 Thionyl chloride (1.93 ml, 26.4 mmol) was added, dropwise, to ice cold ethanol (300 ml), so that the temperature remained below 5 • C. Triglycine (2.50 g, 13.2 mmol) was added, and the solution refluxed for 4 h, under nitrogen. The solvent was removed in vacuo to give a white solid that was recrystallised from boiling ethanol, giving the ester (2.78 g, 83%) as fine white needles.…”

Section: Triglycine Ethyl Ester Hydrochloride (1)mentioning

confidence: 99%

Internally quenched peptides for the study of lysostaphin: an antimicrobial protease that kills Staphylococcus aureus

et al. 2006

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Lysostaphin (EC. 3.4.24.75) is a protein secreted by Staphylococcus simulans biovar staphylolyticus and has been shown to be active against methicillin resistant S. aureus (MRSA). The design and synthesis of three internally quenched substrates for lysostaphin based on the peptidoglycan crossbridges of S. aureus, and their use in fluorescence resonance energy transfer (FRET) assays is reported. These substrates enabled the gathering of information about the endopeptidase activity of lysostaphin and the effect that mutations have on its enzymatic ability. Significant problems with the inner filter effect and substrate aggregation were encountered; their minimisation and the subsequent estimation of the kinetic parameters for the interaction of lysostaphin with the substrates is described, as well as a comparison of substrates incorporating two FRET pairs: Abz-EDDnp and DABCYL-EDANS. In addition to this, the points of cleavage caused by lysostaphin in Abz-pentaglycine-EDDnp have been determined by HPLC and mass spectrometry analysis to be between glycines 2 and 3(approximately 60%) and glycines 3 and 4 (approximately 40%).

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“…Synthesis of ]SN-Enriched Phospholipids. Nitrogen-15labeled DPPC and DPPE were synthesized by transphosphatidylation of commercial DPPC (Sigma) with phospholipase D according to published procedures (Akoka et al, 1985). Phospholipase D was extracted from Brussels sprouts (Davidson & Long, 1958).…”

Section: Methodsmentioning

confidence: 99%

Molecular order, dynamics, and ionization state of phosphatidylethanolamine bilayers as studied by nitrogen-15 NMR

Akoka¹,

Tellier²,

Poignant³

1986

Biochemistry

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Dipalmitoylphosphatidylethanolamine (DPPE) and dipalmitoylphosphatidylcholine (DPPC), 15N-labeled in the polar head group, were synthesized. The proton-decoupled 15N spectra of DPPC and DPPE in aqueous dispersion have exactly the form anticipated for powder line shapes governed by an axially symmetric shielding tensor. The chemical shift anisotropy (delta sigma) of DPPC is lower than 0.4 ppm at 30 degrees C and vanished when the temperature or the half-height line width is increased; DPPE always exhibits an asymmetric line shape, and 15N NMR spectra of DPPE are obtained at various temperatures and simulated to measure exactly the chemical shift anisotropy. At each temperature, the order parameter of the C-N bond segment is derivated from delta sigma and reveals that the average orientation of the C-N bond around the axis of rotation is near the "magic angle" (54.7 degrees). Isotropic correlation times are derived from T1, which are higher than values obtained for phosphatidylcholine by other nuclei. Arrhenius plots of T1 and T2 allowed us to calculate the activation energy for the motion of the DPPE and the DPPC C-N bond. The value of this activation energy for the DPPE (53 kJ/mol) is higher than the one found for the DPPC C-N bond (32 kJ/mol). These differences agree with the capacity of the ethanolamine head groups to bind noncovalently to their neighbors in the plane of the membrane surface. A direct titration curve of the amino group is achieved by the variation of the chemical shift with the bulk pH, and the interfacial pKa is calculated to be 11.1.(ABSTRACT TRUNCATED AT 250 WORDS)

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Synthesis of¹⁵Enriched Phospholipids by Transphosphatidylation

Cited by 8 publications

References 2 publications

Push–Pull Mechanism for Lipid Raft Formation

Push–Pull Mechanism for Lipid Raft Formation

Internally quenched peptides for the study of lysostaphin: an antimicrobial protease that kills Staphylococcus aureus

Molecular order, dynamics, and ionization state of phosphatidylethanolamine bilayers as studied by nitrogen-15 NMR

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Synthesis of15Enriched Phospholipids by Transphosphatidylation

Cited by 8 publications

References 2 publications

Push–Pull Mechanism for Lipid Raft Formation

Push–Pull Mechanism for Lipid Raft Formation

Internally quenched peptides for the study of lysostaphin: an antimicrobial protease that kills Staphylococcus aureus

Molecular order, dynamics, and ionization state of phosphatidylethanolamine bilayers as studied by nitrogen-15 NMR

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Synthesis of¹⁵Enriched Phospholipids by Transphosphatidylation