Synthesis of glycolipids

Gigg, Roy

doi:10.1016/0009-3084(80)90060-2

Cited by 50 publications

(8 citation statements)

References 321 publications

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“….Although glyceroglycolipids occur in plants (Gigg, 1980;Quinn et al, 1978), bacteria (Gigg, 1980;Boggs, 1980), and mycoplasma (De Kruijff et al, 1972), their role is not well understood. Recent studies have attempted to elucidate the effect of the carbohydrate head group on the physical properties of biomembranes and model membranes (Wieslander et al, 1978; Lakdar-Ghazal & Tocanne, 1981;Endo et al, 1983; Iwamoto et al, 1982;Hinz et al, 1985) and to interpret the results in terms of effects specific to the membrane surface.…”

mentioning

confidence: 99%

Determination of conformational properties of glycolipid head groups by deuterium NMR of oriented multibilayers

Jarrell¹,

Jovall²,

Giziewicz³

et al. 1987

Biochemistry

110

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The conformations and orientations of the glucose and glycerol moieties of a monoglucosyl lipid in hydrated bilayers have been determined in detail by deuterium nuclear magnetic resonance (2H NMR). Multibilayer membranes of 1,2-di-O-tetradecyl-3-O-(beta-D-glucopyranosyl)glycerol (DTGL), of dimyristoylphosphatidylcholine (DMPC), and of a mixture of DTGL and DMPC were oriented between glass plates. The glucolipid was selectively labeled with deuterium on the pyranose ring and at C3 of glycerol, whereas DMPC was labeled at the C4 position of the sn-2 chain. Quadrupolar splittings were measured as a function of the angle between the bilayer normal and the magnetic field direction. The results establish that the director of motional averaging, the direction about which motion and order are axially symmetric, is the bilayer normal for all the head group, the glycerol backbone, and the hydrophobic core. Segmental order parameters were determined to be 0.45, 0.65, and 0.40, respectively, for the various regions of DTGL in the membranes. The latter results indicate that there is some motion on the time scale of 10(5) s-1 about the C1'(glucose)-O-C3(glycerol) glycosidic bond but that its amplitude is very restricted. Comparison of 1H-decoupled and 1H-coupled 2H NMR spectra of the C3-labeled glycolipid gave estimates of the 2H-2H dipolar coupling between the deuterons at this position. The orientation of the glycerol C3 hydroxymethylene subunit was calculated relative to the bilayer normal, and the C2-C3 bond was found to be tilted away from the bilayer normal by 3 +/- 1 degree.(ABSTRACT TRUNCATED AT 250 WORDS)

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mentioning

confidence: 99%

Determination of conformational properties of glycolipid head groups by deuterium NMR of oriented multibilayers

Jarrell¹,

Jovall²,

Giziewicz³

et al. 1987

Biochemistry

110

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“…(jTlycolipids constitute a class of lipid that occurs in plants, microorganisms, and animals (Gigg, 1980). Glycolipids are most frequently composed of a carbohydrate head group anchored to the membrane through a diacyl-(or dialkyl-) glycerol or a sphingosine residue.…”

mentioning

confidence: 99%

“…Glycolipids are most frequently composed of a carbohydrate head group anchored to the membrane through a diacyl-(or dialkyl-) glycerol or a sphingosine residue. The carbohydrate head group can be relatively simple (e.g., a single sugar residue) or very complex and may be neutral or charged (Gigg, 1980). Carbohydrates at cell surfaces have been implicated in important cellular events such as cell-cell recognition, ligand-receptor interaction [e.g., cholera toxin receptor (Critchley, 1979)], and ion transport (Karlsson, 1977).…”

mentioning

confidence: 99%

Structure and dynamics of a glyceroglycolipid: a deuterium NMR study of head group orientation, ordering, and effect on lipid aggregate structure

Jarrell¹,

Giziewicz²,

Smith³

1986

Biochemistry

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“…The problems associated with naturally occurring glycolipid syntheses rely on: (i) Difficulty in synthesizing the stereo- and region-controlled side chains; (ii) selective reduction of the sugar protecting groups in the presence of the sphingosine unsaturation, isomerization, racemization and/or hydrolysis. Several groups have already reported synthetic glycolipids [ 23 , 24 ].…”

Section: Neoglycolipids (Ngls) and Glycan Microarraysmentioning

confidence: 99%

Recent Development in the Design of Neoglycoliposomes Bearing Arborescent Architectures

2021

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This brief review highlights systematic progress in the design of synthetic glycolipid (neoglycolipids) analogs evolving from the conventional architectures of natural glycosphingolipids and gangliosides. Given that naturally occurring glycolipids are composed of only one hydrophilic sugar head-group and two hydrophobic lipid tails embedded in the lipid bilayers of the cell membranes, they usually require extraneous lipids (phosphatidylcholine, cholesterol) to confer their stability. In order to obviate the necessity for these additional stabilizing ingredients, recent investigations have merged dendrimer chemistry with that of neoglycolipid syntheses. This singular approach has provided novel glycoarchitectures allowing reconsidering the necessity for the traditional one to two hydrophilic/hydrophobic ratio. An emphasis has been provided in the recent design of modular arborescent neoglycolipid syntheses coined glycodendrimersomes.

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Synthesis of glycolipids

Cited by 50 publications

References 321 publications

Determination of conformational properties of glycolipid head groups by deuterium NMR of oriented multibilayers

Determination of conformational properties of glycolipid head groups by deuterium NMR of oriented multibilayers

Structure and dynamics of a glyceroglycolipid: a deuterium NMR study of head group orientation, ordering, and effect on lipid aggregate structure

Recent Development in the Design of Neoglycoliposomes Bearing Arborescent Architectures

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