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Synthesis, Structure, Analysis and Properties of Glycolipids

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Special Issue Information
Keywords
Published Papers

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (20 September 2013) | Viewed by 48151

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Special Issue Editor

Prof. Dr. Paul V. Murphy

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Guest Editor

School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland
Interests: synthesis of tumour cell migration & angiogenesis inhibitors; synthesis of peptidomimetics and bioactive compounds based on carbohydrates; synthesis of natural products & mimics; glycoside rearrangements (anomerisation) and applications; glycolipid synthesis; synthesis of spatially defined glycoclusters

Special Issue Information

Dear Colleagues,

Glycolipids are an important class of glycoconjugates. They are comprised of lipids covalently attached to carbohydrates. Important constituents of glycolipids include glycosphingolipids (GSLs), glyceroglycolipids (GGLs) or diacylglycolipids (DAGs), glycosylphosphatidylinositol (GPI anchors) & lipopolysaccharides (LPs). Such glycolipids can have structural roles, or mediate cell-cell interactions including host-pathogen interactions or they can act as antigens. Areas of current scientific interest include the synthesis of the various types of glycolipids, biological evaluation of glycolipids, the determination of structure-activity relationships and analysis of structure of naturally occurring glycolipids. Possible applications include using naturally occurring glycolipids or their mimics as anti-infective agents or as vaccine adjuvants. The objective of this special issue of Molecules is to highlight recent original research in the area of glycolipids.

Prof. Dr. Paul V. Murphy
Guest Editor

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Keywords

antigen
molecular recognition
inhibitors
cell signalling
synthesis
glycosides
oligosaccharides
glycosphingolipids
GPI anchor
lipopolysaccharide
glyceroglycolipid

Published Papers (6 papers)

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Research

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320 KiB

Open AccessArticle

Synthesis of a 2ꞌꞌ-Deoxy-β-GalCer

by Meena S. Thakur, Archana Khurana, Mitchell Kronenberg and Amy R. Howell

Molecules 2014, 19(7), 10090-10102; https://doi.org/10.3390/molecules190710090 - 10 Jul 2014

Cited by 5 | Viewed by 6501

Abstract

Structural studies of ternary complexes of CD1d/glycosyl ceramides/iNKT cells and CD1d/sulfatide/sulfatide reactive Type II NKT cells have shown how the polar moieties on the glycolipids interact with both the antigen presenting protein (CD1d) and the T cell receptors. However, these structures alone do not reveal the relative importance of these interactions. This study focuses on the synthesis of the previously unknown 2ꞌꞌ-deoxy-β-galactosyl ceramide 2. This glycolipid is also evaluated for its ability to stimulate iNKT cells and sulfatide-reactive Type II NKT cells. Full article

(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)

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715 KiB

Open AccessArticle

Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues

by Stéphanie Combemale, Jean-Norbert Assam-Evoung, Sabrina Houaidji, Rashda Bibi and Véronique Barragan-Montero

Molecules 2014, 19(1), 1120-1149; https://doi.org/10.3390/molecules19011120 - 17 Jan 2014

Cited by 22 | Viewed by 10722

Abstract

Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen’s cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity. Full article

(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)

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610 KiB

Open AccessArticle

Extending the Glucosyl Ceramide Cassette Approach: Application in the Total Synthesis of Ganglioside GalNAc-GM1b

by Miku Konishi, Akihiro Imamura, Kohki Fujikawa, Hiromune Ando, Hideharu Ishida and Makoto Kiso

Molecules 2013, 18(12), 15153-15181; https://doi.org/10.3390/molecules181215153 - 10 Dec 2013

Cited by 12 | Viewed by 7434

Abstract

The development of a novel cyclic glucosyl ceramide cassette acceptor for efficient glycolipid syntheses was investigated. p-Methoxybenzyl (PMB) groups were selected as protecting groups at C2 and C3 of the glucose residue with the aim of improving the functionality of the cassette acceptor. The choice of the PMB group resulted in a loss of β-selectivity, which was corrected by using an appropriate tether to control the spatial arrangement and the nitrile solvent effect. To investigate the effect of linker structure on the β-selectivity of intramolecular glycosylation, several linkers for tethering the glucose and ceramide moiety were designed and prepared, namely, succinyl, glutaryl, dimethylmalonyl, and phthaloyl esters. The succinyl ester linker was the best for accessing the cassette form. The newly designed glucosyl ceramide cassette acceptor was then applied in the total synthesis of ganglioside GalNAc-GM1b. Full article

(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)

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799 KiB

Open AccessArticle

Synthesis and Thermotropic Phase Behavior of Four Glycoglycerolipids

by Wouter F. J. Hogendorf, Vivien Jagalski, Thomas G. Pomorski, Mikael Bols, Marité Cárdenas and Christian M. Pedersen

Molecules 2013, 18(11), 13546-13573; https://doi.org/10.3390/molecules181113546 - 01 Nov 2013

Cited by 6 | Viewed by 6483

Abstract

Four glycoglycerolipids with different head groups have been synthesized and their physicochemical properties studied. The lengths of the head groups from a mono-saccharide to a trisaccharide, in addition to the anomeric stereochemistry for the smaller glycoglycerolipids, have been modified. The synthesis has been optimized to avoid glycerol epimerization and to allow up-scaling. The physicochemical properties of the glycoglycerolipids were studied and a strong de-mixing of the gel-phase, depending on the head-group, was observed. Full article

(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)

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560 KiB

Open AccessArticle

Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation

by Wayne Pilgrim, Ciaran O'Reilly and Paul V. Murphy

Molecules 2013, 18(9), 11198-11218; https://doi.org/10.3390/molecules180911198 - 12 Sep 2013

Cited by 13 | Viewed by 7154

Abstract

Analogues of glycolipids from Spingomonadacaece with O- and S- and SO₂-linkages have been prepared using chelation induced anomerisation promoted by TiCl₄. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells. Full article

(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)

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Review

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764 KiB

Open AccessReview

Stimulation of Natural Killer T Cells by Glycolipids

by Brian L. Anderson, Luc Teyton, Albert Bendelac and Paul B. Savage

Molecules 2013, 18(12), 15662-15688; https://doi.org/10.3390/molecules181215662 - 16 Dec 2013

Cited by 51 | Viewed by 8366

Abstract

Natural killer T (NKT) cells are a subset of T cells that recognize glycolipid antigens presented by the CD1d protein. The initial discovery of immunostimulatory glycolipids from a marine sponge and the T cells that respond to the compounds has led to extensive research by chemists and immunologists to understand how glycolipids are recognized, possible responses by NKT cells, and the structural features of glycolipids necessary for stimulatory activity. The presence of this cell type in humans and most mammals suggests that it plays critical roles in antigen recognition and the interface between innate and adaptive immunity. Both endogenous and exogenous natural antigens for NKT cells have been identified, and it is likely that glycolipid antigens remain to be discovered. Multiple series of structurally varied glycolipids have been synthesized and tested for stimulatory activity. The structural features of glycolipids necessary for NKT cell stimulation are moderately well understood, and designed compounds have proven to be much more potent antigens than their natural counterparts. Nevertheless, control over NKT cell responses by designed glycolipids has not been optimized, and further research will be required to fully reveal the therapeutic potential of this cell type. Full article

(This article belongs to the Special Issue Synthesis, Structure, Analysis and Properties of Glycolipids)

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