Observation of ganglioside lactone formation with CD spectrometry.


: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.


Chem Phys Lipids


Tsuda M,Terabayashi T,Kawanishi Y




Has Abstract


1994-03-31 00:00:00














  • Synthesis and characterization of long-chain 1,2-dioxo compounds.

    abstract::A series of long-chain methyl esters with vicinal oxo groups (1,2-diones; 1,2-diketones) were synthesized by potassium permanganate-based oxidation of methyl esters of mono-unsaturated fatty acids. The presence of two additional carbonyl groups may facilitate the synthesis of other derivatives. The starting materials ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Knothe G

    更新日期:2002-05-01 00:00:00

  • A DSC and FTIR spectroscopic study of the effects of the epimeric coprostan-3-ols and coprostan-3-one on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes: Comparison with their 5-cholesten analogues.

    abstract::We present the results of a comparative differential calorimetric and Fourier transform infrared spectroscopic study of the effect of cholesterol and five analogues on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes. These sterols/steroids differ in both the nature...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Benesch MG,Lewis RN,Mannock DA,McElhaney RN

    更新日期:2015-05-01 00:00:00

  • Inhibitors of sterol synthesis. Synthesis and spectral properties of 3 beta-hydroxy-5 alpha-cholestan-15-one and its 17 beta-epimer and their effects on 3-hydroxy-3-methylglutaryl coenzyme A reductase activity.

    abstract::3 beta-Hydroxy-5 alpha-cholestan-15-one (2a) and its 14 beta-epimer 2b were prepared from 3 beta-acetoxy-5 alpha-cholest-8(14)-ene (3). Hydroboration of 3 at 45-50 degrees C gave a mixture of 5 alpha,14 alpha-cholestane-3 beta,15 alpha-diol and 5 alpha,14 beta-cholestane-3 beta,15 beta-diol, which were separated on si...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Siddiqui AU,Wilson WK,Parish EJ,Gerst N,Pinkerton FD,Schroepfer GJ Jr

    更新日期:1994-10-20 00:00:00

  • In vitro determination of the solubility limit of cholesterol in phospholipid bilayers.

    abstract::Cholesterol has limited solubility in phospholipid bilayers. The solubility limit is strongly dependent on the nature of the lipid with which the cholesterol is mixed while properties of the crystals formed can be modified by phospholipid-cholesterol interactions. In this review we summarize the various methods that h...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Epand RM,Bach D,Wachtel E

    更新日期:2016-09-01 00:00:00

  • A fluorescence quenching study on protoporphyrin IX in a model membrane system.

    abstract::The interaction of protoporphyrin IX (3,7,12,15-tetramethyl-8, 13-divinyl-2,18-porphyrine-dipropionic acid) (PPIX) with unilamellar dimyristoyl-L-alpha-phosphatidylcholine (DMPC) phospholipid vesicles has been studied by means of steady-state fluorescence quenching spectroscopy. The method of fluorescence-quenching-re...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Kuszaj S,Kaszycki P,Wasylewski Z

    更新日期:1996-09-30 00:00:00

  • Self-assembled systems based on novel hydroxyethylated imidazolium-containing amphiphiles: Interaction with DNA decamer, protein and lipid.

    abstract::The study on aggregation capacity of novel imidazolium-containing amphiphiles of 1-(2-hydroxyethyl)alkylimidazolium bromide series and their interaction with bio-objects (DNA decamer, bovine serum albumin, phospholipid) was performed. It was revealed that introduction of hydroxyethyl moiety into the surfactant molecul...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Kuznetsova DA,Gabdrakhmanov DR,Lukashenko SS,Voloshina AD,Sapunova AS,Kashapov RR,Zakharova LY

    更新日期:2019-09-01 00:00:00

  • Genetic control of glycolipid expression.

    abstract::A polymorphic variation of sialic acid species of sialosyllactosylceramide was found in dog erythrocytes. The analysis of the glycolipids in the erythrocytes of the individual dogs in a family of a Japanese breed of dog, Shiba-Inu, showed that the expression of sialosyllactosylceramide containing N-glycolylneuraminic ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Yamakawa T,Suzuki A,Hashimoto Y

    更新日期:1986-12-15 00:00:00

  • Measurement of phospholipase A2 and 1-alkylglycerophosphocholine acetyltransferase activities in stimulated alveolar macrophages by HPLC analysis of NBD-labeled ether lipids.

    abstract::The importance of phospholipases in cellular signaling and 1-alkylglycerophosphocholine acetyltransferase in the formation of platelet-activating factor (PAF) has stimulated demand for methods to measure these enzyme activities in inflammatory cells. Most of the assays currently used rely on radiolabeled substrates. W...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Kleuser B,Meister A,Sternfeld L,Gercken G

    更新日期:1996-01-25 00:00:00

  • The role of the ganglioside lipid moiety in the process of ganglioside-cell interactions.

    abstract::The role of the ceramide moiety of gangliosides, together with the deriving aggregative properties of ganglioside in solution, in the process of ganglioside-cell interactions was studied. The natural GM1(stearoyl) and the synthetic GM1(acetyl), containing the stearoyl and acetyl groups as the acyl moiety, respectively...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Bassi R,Sonnino S

    更新日期:1992-07-01 00:00:00

  • Further studies on the inhibition of sterol biosynthesis in animal cells by 15-oxygenated sterols.

    abstract::The chemical syntheses of a number of C27 15-oxygenated sterols and their derivatives have been pursued to permit evaluation of their activity in the inhibition of sterol biosynthesis in animal cells in culture. Described herein are chemical syntheses of 3 alpha-benzoyloxy-5 alpha-cholest-8(14)-en-15-one, 5 alpha-chol...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Schroepfer GJ Jr,Parish EJ,Kandutsch AA

    更新日期:1979-11-01 00:00:00

  • Mitochondrial cardiolipin/phospholipid trafficking: the role of membrane contact site complexes and lipid transfer proteins.

    abstract::Historically, cellular trafficking of lipids has received much less attention than protein trafficking, mostly because its biological importance was underestimated, involved sorting and translocation mechanisms were not known, and analytical tools were limiting. This has changed during the last decade, and we discuss ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Schlattner U,Tokarska-Schlattner M,Rousseau D,Boissan M,Mannella C,Epand R,Lacombe ML

    更新日期:2014-04-01 00:00:00

  • Low density lipoprotein oxidation by ferritin at lysosomal pH.

    abstract::Oxidation of low density lipoprotein (LDL) has been proposed to be involved in the pathogenesis of atherosclerosis. We have previously shown that LDL can be oxidised by iron in lysosomes. As the iron-storage protein ferritin might enter lysosomes by autophagy, we have investigated the ability of ferritin to catalyse L...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Ojo OO,Leake DS

    更新日期:2018-12-01 00:00:00

  • Comprehensive analysis of the phospholipids and phytosterols in Schisandra chinensis oil by UPLC-Q/TOF- MSE.

    abstract::Characterization of phospholipids (PLs) and phytosterols were determined in Schisandra chinensis (S. chinensis) oil by UPLC-Q/TOF-MSE. The determination process was based on feature fragment information of components generated by the MSE detector. A total of 49 and 39 PLs were identified in S. chinensis oil under nega...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Gao Y,Wu S

    更新日期:2019-07-01 00:00:00

  • Infrared spectroscopy of glycolipids.

    abstract::The application of infrared spectroscopy to the physicochemical characterization of glycolipids as biologically important membrane constituents is described. In this contribution, the analysis of diacyl- and sphingosine-based (cerebroside, ganglioside) oligosaccharides and the class of lipid A-anchored lipooligo- and ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Brandenburg K,Seydel U

    更新日期:1998-11-01 00:00:00

  • Preparation of long-circulating immunoliposomes using PEG-cholesterol conjugates: effect of the spacer arm between PEG and cholesterol on liposomal characteristics.

    abstract::Poly(ethylene glycol)-coated liposomes were prepared with two new synthesised pegylated cholesterol (Chol) derivatives linked via carbamate bond. Poly(ethylene glycol) (PEG) was directly linked to Chol (PEG-Chol) or through a space arm of diaminebutane (PEG-L-Chol). In buffer, the physicochemical properties of PC/Chol...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Carrion C,Domingo JC,de Madariaga MA

    更新日期:2001-11-01 00:00:00

  • Critical temperatures and a critical chain length in saturated diacylphosphatidylcholines: calorimetric, ultrasonic and Monte Carlo simulation study of chain-melting/ordering in aqueous lipid dispersions.

    abstract::Chain-ordering/melting transition in a series of saturated diacylphosphatidylcholines (PCs) in aqueous dispersions have been studied experimentally (calorimetric and ultrasonic techniques) and theoretically (an Ising-like lattice model). The shape of the calorimetric curves was compared with the theoretical data and i...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Kharakoz DP,Panchelyuga MS,Tiktopulo EI,Shlyapnikova EA

    更新日期:2007-12-01 00:00:00

  • Squeezing lipids: NMR characterization of lipoprotein particles under pressure.

    abstract::Determining the particle size and number of lipoprotein components found in blood plasma (HDL, LDL and VLDL) has become an important clinical tool in diagnosing risk of cardiovascular disease. Proton (1H) NMR spectroscopy methods to quantify lipoprotein particle subclasses have been advancing since NMR lineshape analy...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Starich MR,Tang J,Remaley AT,Tjandra N

    更新日期:2020-05-01 00:00:00

  • Effect of membrane phase transition on long-time calcium-induced fusion of phosphatidylserine vesicles.

    abstract::Dynamic light scattering has been used to study the temperature dependence of the extent of long-time calcium-induced fusion of sonicated vesicles composed of various natural and synthetic phosphatidylserine with different acyl chains. The vesicles of each composition are found to exhibit a peak temperature in the vic...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Leung SO,Ho JT

    更新日期:1991-01-01 00:00:00

  • X-ray diffraction studies of lipid phase transitions in cholesterol-rich membranes at sub-zero temperatures.

    abstract::In X-ray diffraction studies of hydrated (greater than 60%) cholesterol/dioleoylphosphatidylcholine mixtures the lipid packing band showed an abrupt transition from liquid crystal-type to gel-type position and definition at a temperature which decreased progressively to almost -50 degrees C as the proportion of choles...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Finean JB,Hutchinson AL

    更新日期:1988-01-01 00:00:00

  • The conformational properties of the antineoplastic ether lipid 1-thiohexadecyl-2-O-methyl-S-glycero-3-phosphocholine.

    abstract::Thio analogs of platelet activating factor (PAF) are of great interest because they exhibit antineoplastic properties both in vitro and in vivo. In contrast to most known anticancer agents, these lipids appear not to act through the synthesis and function of DNA and, therefore, offer a new avenue of approaching cancer...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Mavromoustakos T,Theodoropoulou E,Yang DP,Lin SY,Koufaki M,Makriyannis A

    更新日期:1996-11-01 00:00:00

  • Effect of lipid environment on amyloid fibril formation of human serum amyloid A.

    abstract::Human serum amyloid A (SAA) is a precursor protein of AA amyloidosis and a component of high-density lipoproteins (HDLs), thus it is essential to investigate the amyloid fibril formation of SAA under a lipid environment. We used synthetic fragment peptides corresponding to the N-terminal (residues 1-27) and central (r...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Tanaka M,Nishimura A,Takeshita H,Takase H,Yamada T,Mukai T

    更新日期:2017-01-01 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


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

    更新日期:1988-11-01 00:00:00

  • The first total synthesis of the marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid: a cytotoxic fatty acid to leukemia cells.

    abstract::The recently discovered marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid was synthesized for the first time in six steps (26% overall yield) starting from commercially available methyl 12-methyltridecanoate. The synthetic approach provided enough material to corroborate the structure of the acid, which wa...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Carballeira NM,Cruz H,Orellano EA,González FA

    更新日期:2003-12-01 00:00:00

  • Thermal acoustic radiation from multilamellar vesicles in lipid phase transition.

    abstract::A new acoustical method for the investigation of lipid phase transition is introduced based on the measurement of the thermal acoustic radiation (TAR) inherent in lipids. The TAR of multilamellar vesicles from dipalmitoylphosphatidylcholine (DPPC) and dimyristoylphosphatidylcholine (DMPC) was measured in the megahertz...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Anosov AA,Barabanenkov YN,Kazanskij AS,Less YA,Sharakshane AS

    更新日期:2008-06-01 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


    authors: Barwicz J,Tancrède P

    更新日期:1997-02-28 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


    authors: Paltauf F

    更新日期:1994-12-01 00:00:00

  • Comparison of plasma and erythrocyte membrane fatty acid compositions in patients with end-stage renal disease and type 2 diabetes mellitus.

    abstract:BACKGROUND:In this study, we aimed to compare the serum lipid profile and fatty acid (FA) compositions of erythrocyte membrane (EM) and plasma in three different patient groups (group 1: type 2 diabetes mellitus (T2DM)+end-stage renal disease (ESRD), group 2: ESRD, group 4: T2DM) and healthy controls (group 3) simultan...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Sertoglu E,Kurt I,Tapan S,Uyanik M,Serdar MA,Kayadibi H,El-Fawaeir S

    更新日期:2014-02-01 00:00:00

  • Biosynthesis and characterization of a series of deuterated cis,cis-octadeca-6,9-dienoic acids.

    abstract::[4,4-2H2]-, [5,5-2H2)-, [6-2H]-, [7-2H]-, [8,8-2H2)-, [11,11-2H2]-, [14,14-2H2]- and [18,18,18-2H3]-cis,cis-octadeca-6,9-dienoic (isolinoleic) acid were synthesized by supplementing cultures of the protozoan Tetrahymena with the corresponding deuterated cis-octadeca-9-enoic (oleic) acids. The cultures were harvested, ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Baenziger JE,Smith IC,Hill RJ

    更新日期:1990-04-01 00:00:00

  • Lipid chain mobility and packing in DOPC bilayers at cryogenic temperatures.

    abstract::Low-temperature molecular mobility and packing in biological tissues are important for their survival upon cryopreservation. Electron paramagnetic resonance (EPR) in its pulsed version of electron spin echo (ESE) allows studying stochastic librations of spin-labeled molecules, the type of motion which dominates at low...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Golysheva EA,Dzuba SA

    更新日期:2020-01-01 00:00:00

  • Electrostatics of carboxylated anionic vesicles for improving entrapment capacity.

    abstract::Electrostatic interaction is an important secondary force affecting the structure, stability, and function of lipid vesicles (liposomes). For this study, a negatively charged lipid with carboxylic acid was mixed with phospholipid to produce anionic vesicles. The electrostatics of the carboxylated anionic vesicle (ca. ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Sou K

    更新日期:2011-03-01 00:00:00