Observation of ganglioside lactone formation with CD spectrometry.

Abstract:

:Monolactone (NeuAc1-9NeuAc linkage) formation of a ganglioside, GD1b, was observed at 20 degrees C on solutions ranging in concentration from 0.008 to 1.7 mM and in pH from 2 to 8.1, by following the change of ellipicity at 235 nm, where lactonized gangliosides showed a strong Cotton effect. The lactonization was found to be a first-order reaction in both GD1b and H+ in the initial stage but was affected later by a backward reaction, hydrolysis of the lactone linkage. The rate constant was 0.08 h-1 at pH 3. At this pH the reaction went close to equilibrium in 24 h at approximately 70% lactonization. At pH higher than 5.9 no change was observed in the ellipticity within 30 h, suggesting the possibility that at most 0.6% of the ganglioside lactonized. Lactonization of another ganglioside, GD3, in glacial acetic acid was observed with a 0.2-mm cell, agreeing well with a reported result.

journal_name

Chem Phys Lipids

authors

Tsuda M,Terabayashi T,Kawanishi Y

doi

10.1016/0009-3084(94)90051-5

subject

Has Abstract

pub_date

1994-03-31 00:00:00

pages

95-9

issue

1

eissn

0009-3084

issn

1873-2941

pii

0009-3084(94)90051-5

journal_volume

70

pub_type

杂志文章
  • Mitochondrial alterations in apoptosis.

    abstract::Besides their conventional role as energy suppliers for the cell, mitochondria in vertebrates are active regulators of apoptosis. They release apoptotic factors from the intermembrane space into the cytosol through a mechanism that involves the Bcl-2 protein family, mediating permeabilization of the outer mitochondria...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/j.chemphyslip.2014.04.001

    authors: Cosentino K,García-Sáez AJ

    更新日期:2014-07-01 00:00:00

  • Synthesis and proaggregatory activity of 1-O-(2-methyloctadecyl)-2-O-acetyl-rac-glycero-3-phosphocholine.

    abstract::Racemic 1-O-(2-methyloctadecyl)-2-O-acetyl-glycero-3-phosphocholine, a branched chain PAF species, was prepared by chemical synthesis and investigated for biological activity on human blood platelets in vitro. The synthesis started from 2-O-benzylglycerol and 2-methyloctadecyl-1-methyl sulfonate and was accomplished i...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(91)90017-6

    authors: Schmid B,Ostermann G,Kertscher HP

    更新日期:1991-11-01 00:00:00

  • Structure, supramolecular organization and thermotropic phase behavior of N-acyl tris homologs (n = 9-18): Structural analogs of apoptosis inducing ceramides.

    abstract::N-Acyl tris(hydroxymethyl)aminomethanes (N-acyl tris, NATs) are structural analogs of ceramides, which were reported to induce apoptosis either by elevation of ceramide levels or by activation of pro-apoptotic effectors that are physiological targets of ceramide. In this study, we synthesized and characterized a homol...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2018.10.002

    authors: D S,Ravindar C,Swamy MJ

    更新日期:2018-12-01 00:00:00

  • Does cholesterol discriminate between sphingomyelin and phosphatidylcholine in mixed monolayers containing both phospholipids?

    abstract::The objective of this work was to examine the interaction of cholesterol with both phosphatidylcholines, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) or 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and sphingomyelins, N-oleoyl-D-sphingomyelin (O-SPM) or N-palmitoyl-D-sphingomyelin (P-SPM), in monolay...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(96)02535-2

    authors: Mattjus P,Slotte JP

    更新日期:1996-06-17 00:00:00

  • Cardiolipin metabolism and its causal role in the etiology of the inherited cardiomyopathy Barth syndrome.

    abstract::Cardiolipin (CL) is a phospholipid with many unique characteristics. CL is synthesized in the mitochondria and resides almost exclusively within the mitochondrial inner membrane. Unlike most phospholipids that have two fatty acyl chains, CL possesses four fatty acyl chains resulting in unique biophysical characteristi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/j.chemphyslip.2015.09.005

    authors: Gaspard GJ,McMaster CR

    更新日期:2015-12-01 00:00:00

  • Hypochlorous acid-induced stress on human spermatozoa. A model for inflammation in the male genital tract.

    abstract::The fertilising ability of human spermatozoa may be impaired by inflammations of the genital tract, although details of these processes are still unknown. Hypochlorous acid (HOCl), an important product of myeloperoxidase released from stimulated neutrophils, induces a concentration-dependent increase in externalisatio...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2005.02.015

    authors: Lessig J,Gey C,Schiller J,Süss R,Paasch U,Grunewald S,Glander HJ,Arnhold J

    更新日期:2005-06-01 00:00:00

  • The replacement of cholesterol by phytosterols and the increase of total sterol content in model erythrocyte membranes.

    abstract::The activity of phytosterols on human organism includes the ability of these compounds to incorporate into membranes. In the consequence the plant sterols are able to increase total sterol concentration in membrane or/and to replace cholesterol molecules. The aim of this work was to compare the influence of both these...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2010.07.001

    authors: Hac-Wydro K

    更新日期:2010-09-01 00:00:00

  • A particle concentration fluorescence immunoassay for Lp(a).

    abstract::The quantitation of Lp(a) by immunoassay presents a major technical problem, because the molecular mass of the (a) protein of Lp(a) can vary between 419,000 and 838,000 Da (Gaubatz et al. (1990) J. Lipid Res. 31, 603-612), and this variability is determined by at least 24 alleles of the (a) gene. In an attempt to over...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90144-9

    authors: Kottke BA,Bren ND

    更新日期:1994-01-01 00:00:00

  • Spontaneous vesiculation of uncharged phospholipid dispersions consisting of lecithin and lysolecithin.

    abstract::The work presented here demonstrates that the phenomenon of spontaneous vesiculation is not restricted to charged lipids and lipid mixtures, but occurs also in isoelectric phospholipid mixtures consisting of egg phosphatidylcholine (EPC) and egg lysophosphatidylcholine (lyso-EPC). 1H high-resolution NMR and freeze-fra...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(87)90024-7

    authors: Hauser H

    更新日期:1987-05-01 00:00:00

  • Preparation of omega-functionalized eicosane-phosphate building blocks.

    abstract::New 1,20-substituted eicosanes carrying phosphate headgroups and readily derivatizable thiol, maleimido, and activated carboxylic ester moieties were prepared. The C20-backbone of these molecules was assembled by a halopolycarbon homologation from 1,8-dichlorooctane and 1,6-dibromohexane. 20-Mercapto- and 20-maleimido...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2004.09.016

    authors: Jablonkai I,Oroszlan P

    更新日期:2005-01-01 00:00:00

  • Copper-induced peroxidation of phosphatidylserine-containing liposomes is inhibited by nanomolar concentrations of specific antioxidants.

    abstract::Copper-induced peroxidation of liposomal palmitoyllinoleoyl-phosphatidylcholine (PLPC) is inhibited by alpha-tocopherol at micromolar concentrations. In our previous study we found that when the liposomes contain phosphatidylserine (PS), nanomolar concentrations of Toc were sufficient to inhibit peroxidation. In an at...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2007.08.001

    authors: Gal S,Lichtenberg D,Bor A,Pinchuk I

    更新日期:2007-12-01 00:00:00

  • Liquid crystal-based capillary sensory platform for the detection of bile acids.

    abstract::Bile acids directly related to liver and intestinal function are used as indicators of hepatobiliary and intestinal diseases. Here, we have designed and realized a capillary sensory platform for the detection of bile acids using liquid crystals (LCs). LC droplets confined in micro-capillaries are homeotropically align...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2017.02.003

    authors: Kim HJ,Jang CH

    更新日期:2017-04-01 00:00:00

  • Role of Rutin Nanoemulsion in Ameliorating Oxidative Stress: Pharmacokinetic and Pharmacodynamics Studies.

    abstract::Parkinson's disease is caused due to free radical generation in dopamine neurons leading to oxidative stress induced damage. The aim of this work was to ameliorate the free radical induced oxidative stress in rats by using TPGS (Tocopheryl polyethylene glycol 1000 succinate) loaded rutin nanoemulsion after oral admini...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2020.104890

    authors: Sharma S,Rabbani SA,Narang JK,Hyder Pottoo F,Ali J,Kumar S,Baboota S

    更新日期:2020-05-01 00:00:00

  • Translational diffusion measurements of a fluorescent phospholipid between MDCK-I cells support the lipid model of the tight junctions.

    abstract::The diffusion of a lipid fluorescent analogue across tight junctions in MDCK-I cells was studied by FRAP measurements. Cells were labelled with C6-NBD-PC at the apical cell membrane. Transepithelial resistance of MDCK-I cells was found to be higher than 3000 omega x cm2, which indicates the presence of a very tight ep...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90066-3

    authors: Grebenkämper K,Galla HJ

    更新日期:1994-05-23 00:00:00

  • Structural and dynamic insights on the EmrE protein with TPP+ and related substrates through molecular dynamics simulations.

    abstract::EmrE is a bacterial transporter protein that forms an anti-parallel homodimer with four transmembrane helices in each monomer. EmrE transports positively charged aromatic compounds, such as TPP+ and its derivatives. We performed molecular dynamics (MD) simulations of EmrE in complex with TPP+, MeTPP+, and MBTPP+ embed...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2017.12.004

    authors: Padariya M,Kalathiya U,Baginski M

    更新日期:2018-05-01 00:00:00

  • Fluorescence studies of lipid regular distribution in membranes.

    abstract::This article reviews the use of fluorescent lipids and free probes in the studies of lipid regular distribution in model membranes. The first part of this article summarizes the evidence and physical properties for lipid regular distribution in pyrene-labeled phosphatidylcholine (PC)/unlabeled PC binary mixtures as re...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/s0009-3084(02)00025-7

    authors: Chong PL,Sugár IP

    更新日期:2002-06-01 00:00:00

  • Sterol synthesis. A novel reductive rearrangement of an alpha,beta-unsaturated steroidal epoxide; a new chemical synthesis of 5alpha-cholest-8(14)-en-3beta, 15alpha-diol.

    abstract::Reduction of 3beta-benzoyloxy-14alpha,15alpha-epoxy-5alpha-cholest-7-ene with either lithium triethylboro-hydride or lithium aluminum hydride (4 molar excess) gave 5-alpha-cholest-8(14)-en-3beta,15alpha-diol in high yield. Reduction of the epoxy ester with lithium triethylborodeuteride or lithium aluminum deuteride (4...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(77)90013-5

    authors: Parish EJ,Schroepfer GJ Jr

    更新日期:1977-04-01 00:00:00

  • The interaction of water with the phospholipid head group and its relationship to the lipid electrical conductivity.

    abstract::We have studied the interaction of water with the lipid head group by gravimetrically measuring the lipid water adsorption and the lateral dc electrical conductivity increase resulting from this hydration. We have done this for dimyristoyl phosphatidylcholine (DMPC) having protonated or deuterated hydrocarbon chains. ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2004.05.003

    authors: Jendrasiak GL,Smith RL

    更新日期:2004-09-01 00:00:00

  • Effect of lipoprotein(a) on lipid metabolism of cultured human intimal aortic cells.

    abstract::The effect of Lp(a) on lipid metabolism in cells cultured from unaffected human aortic intima has been investigated. Lp(a) isolated from the blood of healthy subjects failed to alter intracellular neutral lipid content. On the other hand, Lp(a) obtained from coronary atherosclerosis patients induced a 1.5- to 2-5-fold...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90135-x

    authors: Tertov VV,Orekhov AN

    更新日期:1994-01-01 00:00:00

  • Changes induced in bovine serum albumin following interactions with the lipid peroxidation product E-2-octenal.

    abstract::Bovine serum albumin (BSA) undergoes a number of deteriorative changes when exposed to E-2-octenal. Reaction of BSA with E-2-octenal produced fluorescent BSA with an excitation maximum at 350 nm and emission maximum at 440 nm and promoted polymerization. Amino acid analysis of the modified BSA showed that the E-2-octe...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(95)02470-4

    authors: Alaiz M,Barragán S

    更新日期:1995-08-25 00:00:00

  • The effect of aggregation state of amphotericin-B on its interactions with cholesterol- or ergosterol-containing phosphatidylcholine monolayers.

    abstract::Amphotericin B (AmB) is the most effective antibiotic used in the treatment of systemic fungal infections. It is generally thought that the activity of this drug results from its interaction with ergosterol, the main sterol of fungi membranes. However, AmB also interacts with cholesterol, the major sterol of mammal me...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(96)02652-7

    authors: Barwicz J,Tancrède P

    更新日期:1997-02-28 00:00:00

  • Aminoglycoside antibiotics prevent the formation of non-bilayer structures in negatively-charged membranes. Comparative studies using fusogenic (bis(beta-diethylaminoethylether)hexestrol) and aggregating (spermine) agents.

    abstract::Aminoglycoside antibiotics cause aggregation but not fusion of negatively-charged liposomes at an extent proportional to their capacity to interact with acidic phospholipids (Van Bambeke et al., 1995, Eur. J. Pharmacol., 289, 321-333). To understand why aggregation is not followed by fusion, we have examined here the ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(95)02520-0

    authors: van Bambeke F,Mingeot-Leclercq MP,Brasseur R,Tulkens PM,Schanck A

    更新日期:1996-03-29 00:00:00

  • Synthesis of the 3-sulfates of S-acyl glutathione conjugated bile acids and their biotransformation by a rat liver cytosolic fraction.

    abstract::The 3-sulfates of the S-acyl glutathione (GSH) conjugates of five natural bile acids (cholic, chenodeoxycholic, deoxycholic, ursodeoxycholic, and lithocholic) were synthesized as reference standards in order to investigate their possible formation by a rat liver cytosolic fraction. Their structures were confirmed by p...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2012.02.001

    authors: Mitamura K,Hori N,Mino S,Iida T,Hofmann AF,Ikegawa S

    更新日期:2012-04-01 00:00:00

  • Synthesis of racemic 2,4-dimethyltetradecanoic acid from Mycobacterium kansasii.

    abstract::A known intermediate, (3 R, S; 5 R,S)-3,5-dimethyl-6-triphenylmethyloxyhexanal gave, in a Wittig reaction with 1-octyltriphenylphosphonium bromide and n-butyl lithium in anhydrous tetrahydrofuran, a mixture of olefininic compounds. Trityl deprotection and hydrogenation of the double bond afforded the (2 R, S; 4 R,S)-2...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(96)02570-4

    authors: Wallace PA,Minnikin DE

    更新日期:1996-08-19 00:00:00

  • Ether lipids in biomembranes.

    abstract::Plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) and to a lesser extent the 1-O-alkyl analogs are ubiquitous and in some cases major constituents of mammalian cellular membranes and of anaerobic bacteria. In archaebacteria polar lipids of the cell envelope are either diphytanylglycerolipids or bipolar macrocyc...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/0009-3084(94)90054-x

    authors: Paltauf F

    更新日期:1994-12-01 00:00:00

  • Vitamin E - phosphatidylethanolamine interactions in mixed membranes with sphingomyelin: Studies by 2H NMR.

    abstract::Among the structurally diverse collection of lipids that comprise the membrane lipidome, polyunsaturated phospholipids are particularly vulnerable to oxidation. The role of α-tocopherol (vitamin E) is to protect this influential class of membrane phospholipid from oxidative damage. Whether lipid-lipid interactions pla...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2020.104910

    authors: Cavazos AT,Kinnun JJ,Williams JA,Wassall SR

    更新日期:2020-09-01 00:00:00

  • Fluid phase structure of EPC and DMPC bilayers.

    abstract::X-ray diffraction data taken at high instrumental resolution were obtained for EPC and DMPC under various osmotic pressures, primarily at T = 30 degrees C. The headgroup thickness DHH was obtained from relative electron density profiles. By using volumetric results and by comparing to gel phase DPPC we obtain areas AE...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(98)00068-1

    authors: Petrache HI,Tristram-Nagle S,Nagle JF

    更新日期:1998-09-01 00:00:00

  • Synthesis and photochemical properties of PEGylated coumarin-caged ceramides for cell studies.

    abstract::Caged ceramide analogues (C6-, C16-, C18-, C22- and C24-Cer) have been prepared by introducing a hydrophilic coumarin-based cage bearing a short polyethylene glycol (PEG) chain. (6-Bromo-7-mTEGylated-coumarin-4-yl)methyl (Btc) caged ceramide showed efficient photo-uncaging to release the parent ceramide upon direct ex...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2015.07.006

    authors: Kim YA,Day J,Lirette CA,Costain WJ,Johnston LJ,Bittman R

    更新日期:2016-01-01 00:00:00

  • Structure of polymerizable lipid bilayers. I--1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine, a tubule-forming phosphatidylcholine.

    abstract::This report presents the first X-ray diffraction data on diacetylenic phospholipids. The tubule-forming polymerizable lipid, 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine (DC8,9PC), was studied by low angle X-ray diffraction from partially dehydrated oriented multibilayers in both polymerized and unpolymer...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(88)90062-x

    authors: Rhodes DG,Blechner SL,Yager P,Schoen PE

    更新日期:1988-11-01 00:00:00

  • Characterization of liposomes and other lipid assemblies by multiprobe fluorescence polarization.

    abstract::This minireview describes the use of fluorescence polarization to characterize the dynamics and organization of biological membranes, lipoproteins, liposomes and other lipid-based assemblies. The advantages, disadvantages and limitations of this method are discussed. There is special emphasis on the multiprobe approac...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/0009-3084(93)90061-7

    authors: Borenstain V,Barenholz Y

    更新日期:1993-09-01 00:00:00