Carbohydrate liquid crystals: synthesis and characterisation of the methyl-6-O-(n-acyl)-α-D-glucopyranosides.


:Seven members of the methyl-6-O-(n-acyl)-α-D-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. Variable temperature infrared spectroscopy reveals that the hydrogen bonding within the system shows a marked change at the melting point but apparently no change at the smectic A-isotropic transition. This observation is interpreted in terms of Goodby's model for the smectic A phase in which the carbohydrate moieties are located at the centre of the smectic bilayer and assuming that hydrogen bonded aggregates persist into the isotropic phase. Within this framework, the unusually low values of the entropy change associated with the smectic A-isotropic transition may also be accounted for.


Chem Phys Lipids


Cook AG,Wardell JL,Imrie CT




Has Abstract


2011-02-01 00:00:00














  • Determinants of F2-isoprostane biosynthesis and inhibition in man.

    abstract::Several cardiovascular risk factors are characterized by the coexistence of low-grade inflammation, enhanced oxidative stress and lipid peroxidation. It has been hypothesized that F2-isoprostanes, a product of in vivo lipid peroxidation, may transduce the effects of metabolic and hemodynamic abnormalities into increas...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Davì G,Falco A,Patrono C

    更新日期:2004-03-01 00:00:00

  • Pathways of cholesterol oxidation via non-enzymatic mechanisms.

    abstract::Cholesterol has many functions, including those that affect biophysical properties of membranes, and is a precursor to hormone synthesis. These actions are governed by enzymatic pathways that modify the sterol nucleus or the isooctyl tail. The addition of oxygen to the cholesterol backbone produces its derivatives kno...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Iuliano L

    更新日期:2011-09-01 00:00:00

  • Evaluation of products upon the reaction of hypohalous acid with unsaturated phosphatidylcholines.

    abstract::Myeloperoxidase released from stimulated neutrophils is able to produce hypochlorous and hypobromous acids. The composition of the reaction products of the interaction of hypohalous acid with double bonds of phosphatidylcholines was analysed by matrix-assisted laser desorption/ionisation time-of-flight mass spectromet...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Spalteholz H,Wenske K,Panasenko OM,Schiller J,Arnhold J

    更新日期:2004-04-01 00:00:00

  • Insights on the interaction of met-enkephalin with negatively charged membranes--an infrared and solid-state NMR spectroscopic study.

    abstract::Enkephalins are pentapeptides found in the human nervous system, where they are involved in the relief of pain. The interaction of these neuropeptides with the nerve cell membranes would be a key-step in the receptor binding. We have used both Fourier-transform infrared and solid-state NMR spectroscopies to shed light...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Marcotte I,Ouellet M,Auger M

    更新日期:2004-02-01 00:00:00

  • Influence of lipids with hydroxyl-containing head groups on Fe2+ (Cu2+)/H2O2-mediated transformation of phospholipids in model membranes.

    abstract::Under condition of ROS formation in lipid membranes, free radical reactions can proceed in both hydrophobic (peroxidation of lipids, POL) and polar (free radical fragmentation) parts of the bilayer. Free-radical fragmentation is typical for the lipids containing a hydroxyl group in β-position with respect to an ester ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Olshyk VN,Melsitova IV,Yurkova IL

    更新日期:2014-01-01 00:00:00

  • Analogs of natural lipids. II. Polymorphic behavior of the tris-homoacyl derivatives of cyclopentane-1,2,3-triols.

    abstract::The polymorphic behavior of three series of tris-homoacyl (C14:0, C16:0 and C18:0) cyclopentane-1,2,3-triol analogs of the natural saturated triglycerides has been studied using differential thermal analysis, Fourier transform infrared spectroscopy, and X-ray diffraction. It was found that the triglyceride analogs der...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Greenwald SM,Hancock AJ,Sable HZ,D'Esposito L,Koenig JL

    更新日期:1977-03-01 00:00:00

  • 1-O-benzyl-2-O-methyl-rac-glycerol: a key intermediate for synthesis of ether glycerolipids.

    abstract::A new scheme for synthesis of saturated 1-O-alkyl-2-O-methyl-rac-glycerolipids is described. The reductive cleavage of 2-O-methyl-1,3-O,O-benzylideneglycerol with BH3.THF complex leads to 1-O-benzyl-2-O-methyl-rac-glycerol, which is a key in intermediate for the facile preparation of 1-O-alkyl-2-O-methyl-rac-glycerol ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Pinchuk AN,Mitsner BI,Shvets VI

    更新日期:1991-10-01 00:00:00

  • Lipid profiles in brains from sheep with natural scrapie.

    abstract::Prion diseases are fatal neurodegenerative disorders affecting many mammals, ovine scrapie being the archetypal prion disease. Several independent studies in murine and cell-based models of scrapie have highlighted the presence of a link between prion generation and lipid alterations; yet, no data on natural disease a...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Rosa A,Scano P,Incani A,Pilla F,Maestrale C,Manca M,Ligios C,Pani A

    更新日期:2013-10-01 00:00:00

  • Antioxidant effects of green tea polyphenols on free radical initiated peroxidation of rat liver microsomes.

    abstract::Antioxidative effects of the principal polyphenolic components extracted from green tea leaves, i.e. (-)-epicatechin (EC), (-)-epicatechin gallate (ECG), (-)-epigallocatechin gallate (EGCG), (-)-epigallocatechin (EGC), and gallic acid (GA), against free radical initiated peroxidation of rat liver microsomes were studi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Cai YJ,Ma LP,Hou LF,Zhou B,Yang L,Liu ZL

    更新日期:2002-12-01 00:00:00

  • Cationic lipids for gene delivery: many players, one goal.

    abstract::Lipid-based carriers represent the most widely used alternative to viral vectors for gene expression and gene silencing purposes. This class of non-viral vectors is particularly attractive for their ease of synthesis and chemical modifications to endow them with desirable properties. Despite combinatorial approaches h...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Ponti F,Campolungo M,Melchiori C,Bono N,Candiani G

    更新日期:2021-01-08 00:00:00

  • Raman spectroscopy investigation of various saturated monoacid triglycerides.

    abstract::A study of the vibrational behavior of five saturated monoacid triacylglycerides is performed by Raman spectroscopy at room temperature in the 3100-500 cm(-1) spectral range. The splitting of the CO stretching mode leads to conclude on the existence of two or three geometries of CO in the "knot" group OCO. The CO stre...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Bresson S,El Marssi M,Khelifa B

    更新日期:2005-04-01 00:00:00

  • Macrophage sphingolipids are essential for the entry of mycobacteria.

    abstract::Mycobacteria are intracellular pathogens that can invade and survive within host macrophages. Mycobacterial infections remain a major cause of mortality and morbidity worldwide, with serious concerns of emergence of multi and extensively drug-resistant tuberculosis. While significant advances have been made in identif...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Viswanathan G,Jafurulla M,Kumar GA,Raghunand TR,Chattopadhyay A

    更新日期:2018-07-01 00:00:00

  • Lipid transfer proteins and the tuning of compartmental identity in the Golgi apparatus.

    abstract::The Golgi complex constitutes a central way station of the eukaryotic endomembrane system, an intricate network of organelles engaged in control of membrane trafficking and the processing of various cellular components. Previous ideas of compartmental stability within this network are gradually being reshaped by conce...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: McDermott MI,Mousley CJ

    更新日期:2016-10-01 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

  • Changes in the components of biliary and plasma lipids in selenium-deficient rats.

    abstract::We constructed a chronic oxidative stress model in which Se-deficient diet was fed to male Wister rats for 8 weeks. As expected, effects of oxidative damage, including Fe accumulation and increase in peroxidized lipids, were identified in the liver owing to the lack of glutathione peroxidase. Although the oxidative st...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Sakuma Y,Sasaki J,Futami A,Yamasaki K,Matsuoka K,Honda C,Endo K,Tsukada M

    更新日期:2007-08-01 00:00:00

  • Aggregate formation in the intercalation of long-chain fatty acid esters into liposomes.

    abstract::Various hydrophobic benzenediacetic esters, the corresponding benzenedipropionic esters, and branched alkyl esters were intercalated into DMPC liposomes, where the molar ratio (n/n) of ester:DMPC was 1:5. In the case of the very long-chain derivatives, double carbonyl peaks were observed in the 13C NMR spectrum. This ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Cohen Y,Afri M,Frimer AA

    更新日期:2008-10-01 00:00:00

  • 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


    authors: Cosentino K,García-Sáez AJ

    更新日期:2014-07-01 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


    authors: Chong PL,Sugár IP

    更新日期:2002-06-01 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


    authors: Wallace PA,Minnikin DE

    更新日期:1996-08-19 00:00:00

  • Improvising anti-leishmanial activity of amphotericin B and paromomycin using co-delivery in d-α-tocopheryl polyethylene glycol 1000 succinate (TPGS) tailored nano-lipid carrier system.

    abstract::In the current study, we have focused on the design, development and in-vitro evaluation of d-α-tocopheryl polyethylene glycol 1000 succinate modified amphotericin B (AmB) and paromomycin (PM) loaded solid lipid nanoparticles (TPGS-SLNPs) by emulsion-solvent evaporation method. The optimized TPGS-SLNPs had a mean part...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Parvez S,Yadagiri G,Singh A,Karole A,Singh OP,Sundar S,Mudavath SL

    更新日期:2020-09-01 00:00:00

  • Polymerizable phospholipids with lipoic acid as head group: synthesis and phase properties.

    abstract::Lipoic acid-substituted phospholipids were synthesized from phosphatidyl cholines by exchanging the choline residue with a glycol group using phospholipase D, forming phosphatidylglycols, and coupling of lipoic acid (1,2-dithiolane-3-pentanoic acid) to the residual glycol hydroxyl group by esterification. The thermotr...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Pax H,Blume A

    更新日期:1993-11-01 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


    authors: Hauser H

    更新日期:1987-05-01 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

  • 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

  • Thermodynamic and structural effects of propranolol on DPPC liposomes.

    abstract::Some thermodynamic and structural aspects of propranolol-DPPC liposomes interaction were investigated by DSC and X-ray diffraction: the lamellar arrangement of the lipid matrix remains intact even at high concentrations of the drug (until 1:1 drug/lipid molar ratio). However, the bilayer thickness increases significan...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Albertini G,Donati C,Phadke RS,Ponzi Bossi MG,Rustichelli F

    更新日期:1990-09-01 00:00:00

  • The phase transition behavior of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) model membrane influenced by 2,4-dichlorophenol--an FT-Raman spectroscopy study.

    abstract::The effect of 2,4-dichlorophenol (DCP) on the structures and phase transitions of fully hydrated 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) liposomes was studied using FT-Raman spectroscopy. Whereas the Raman frequency shifts of the most frequently investigated bands of C-C and C-H stretching regions only indi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Csiszár A,Koglin E,Meier RJ,Klumpp E

    更新日期:2006-02-01 00:00:00

  • Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system II - 13C NMR relaxation study.

    abstract::The addition of hydrophilic and hydrophobic molecules to the 1-monooleoyl glycerol (MO)/water (W) system has been investigated at a molecular level by 13C nuclear magnetic resonance (NMR) relaxation. Depending on the nature of the additive, the liquid crystalline phases of the MO/W binary system are modified. The 13C ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Murgia S,Caboi F,Monduzzi M

    更新日期:2001-03-01 00:00:00

  • Phase state and surface topography of palmitoyl-ceramide monolayers.

    abstract::In cell biology (and in many biophysical) studies there is a natural tendency to consider ceramide as a highly condensed, solid-type lipid conferring rigidity and close packing to biomembranes. In the present work we advanced the understanding of the phase behavior of palmitoyl-ceramide restricted to a planar interfac...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Fanani ML,Maggio B

    更新日期:2010-06-01 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


    authors: Alaiz M,Barragán S

    更新日期:1995-08-25 00:00:00

  • The effects of Ca2+ on lipid diffusion.

    abstract::The effects of Ca2+ on rotational and translational diffusion of lipids in multilamellar dimyristoylphosphatidylcholine (DMPC)-water systems were investigated by time-resolved phosphorescence anisotropy steady-state fluorescence polarization and fluorescence recovery after photobleaching (FRAP) experiments. Above the ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Blatt E,Vaz WL

    更新日期:1986-10-01 00:00:00