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Special Issue "Synthesis, Structure, Analysis and Properties of Glycolipids"

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

Deadline for manuscript submissions: closed (20 September 2013)

Special Issue Editor

Guest Editor
Prof. Dr. Paul V. Murphy (Website)

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

Submission

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. Papers will be published continuously (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are refereed through a peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed Open Access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs).

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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Open AccessArticle Synthesis of a 2ꞌꞌ-Deoxy-β-GalCer
Molecules 2014, 19(7), 10090-10102; doi:10.3390/molecules190710090
Received: 29 May 2014 / Revised: 25 June 2014 / Accepted: 30 June 2014 / Published: 10 July 2014
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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 [...] Read more.
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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Open AccessArticle Gold Nanoparticles Decorated with Mannose-6-phosphate Analogues
Molecules 2014, 19(1), 1120-1149; doi:10.3390/molecules19011120
Received: 25 November 2013 / Revised: 7 January 2014 / Accepted: 10 January 2014 / Published: 17 January 2014
Cited by 3 | PDF Full-text (715 KB) | HTML Full-text | XML Full-text
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 [...] Read more.
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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Open AccessArticle Extending the Glucosyl Ceramide Cassette Approach: Application in the Total Synthesis of Ganglioside GalNAc-GM1b
Molecules 2013, 18(12), 15153-15181; doi:10.3390/molecules181215153
Received: 7 November 2013 / Revised: 1 December 2013 / Accepted: 2 December 2013 / Published: 10 December 2013
Cited by 3 | PDF Full-text (610 KB) | HTML Full-text | XML Full-text
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 [...] Read more.
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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Open AccessArticle Synthesis and Thermotropic Phase Behavior of Four Glycoglycerolipids
Molecules 2013, 18(11), 13546-13573; doi:10.3390/molecules181113546
Received: 16 September 2013 / Revised: 15 October 2013 / Accepted: 19 October 2013 / Published: 1 November 2013
Cited by 3 | PDF Full-text (799 KB) | HTML Full-text | XML Full-text | Supplementary Files
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 [...] Read more.
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)
Open AccessArticle Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation
Molecules 2013, 18(9), 11198-11218; doi:10.3390/molecules180911198
Received: 31 July 2013 / Revised: 4 September 2013 / Accepted: 5 September 2013 / Published: 12 September 2013
Cited by 3 | PDF Full-text (560 KB) | HTML Full-text | XML Full-text
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 [...] Read more.
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

Jump to: Research

Open AccessReview Stimulation of Natural Killer T Cells by Glycolipids
Molecules 2013, 18(12), 15662-15688; doi:10.3390/molecules181215662
Received: 4 November 2013 / Revised: 11 December 2013 / Accepted: 11 December 2013 / Published: 16 December 2013
Cited by 16 | PDF Full-text (764 KB) | HTML Full-text | XML Full-text
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 [...] Read more.
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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