Novel approach to the study of the antigenicities and receptor functions of carbohydrate chains of glycoproteins

Tang, Ping; Gool, H.C.; Hardy, Mark R.; Lee, Y.C.; Felzi, Ten

doi:10.1016/0006-291x(85)91158-1

Cited by 125 publications

(37 citation statements)

References 37 publications

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“…Neoglycolipid (NGL) technology was introduced to glycoconjugate research in 1985 to enable binding studies to be conveniently executed with oligosaccharides of glycoproteins (Tang et al, 1985). The approach that was chosen by Feizi and co-workers was chemical conjugation of oligosaccharides after release from the carrier glycoprotein to a lipid anchor generating artificial glycolipids, neoglycolipids (NGLs), reviewed by Feizi et al (1994) and Chai et al (2003b).…”

Section: Tlc-ms Of Neoglycolipidsmentioning

confidence: 99%

Advances on the compositional analysis of glycosphingolipids combining thin-layer chromatography with mass spectrometry

Müthing

Distler

2009

Mass Spectrom. Rev.

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Glycosphingolipids (GSLs), composed of a hydrophilic carbohydrate chain and a lipophilic ceramide anchor, play pivotal roles in countless biological processes, including infectious diseases and the development of cancer. Knowledge of the number and sequence of monosaccharides and their anomeric configuration and linkage type, which make up the principal items of the glyco code of biologically active carbohydrate chains, is essential for exploring the function of GSLs. As part of the investigation of the vertebrate glycome, GSL analysis is undergoing rapid expansion owing to the application of novel biochemical and biophysical technologies. Mass spectrometry (MS) takes part in the network of collaborations to further unravel structural and functional aspects within the fascinating world of GSLs with the ultimate aim to better define their role in human health and disease. However, a single-method analytical MS technique without supporting tools is limited yielding only partial structural information. Because of its superior resolving power, robustness, and easy handling, high-performance thin-layer chromatography (TLC) is widely used as an invaluable tool in GSL analysis. The intention of this review is to give an insight into current advances obtained by coupling supplementary techniques such as TLC and mass spectrometry. A retrospective view of the development of this concept and the recent improvements by merging (1) TLC separation of GSLs, (2) their detection with oligosaccharide-specific proteins, and (3) in situ MS analysis of protein-detected GSLs directly on the TLC plate, are provided. The procedure works on a nanogram scale and was successfully applied to the identification of cancer-associated GSLs in several types of human tumors. The combination of these two supplementary techniques opens new doors by delivering specific structural information of trace quantities of GSLs with only limited investment in sample preparation.

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Section: Tlc-ms Of Neoglycolipidsmentioning

confidence: 99%

Advances on the compositional analysis of glycosphingolipids combining thin-layer chromatography with mass spectrometry

Müthing

Distler

2009

Mass Spectrom. Rev.

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“…After cleaving all the ester bonds including the lactone ring of 4 with an alkaline solution, the olefin bond in the pentenyl group of 4 was ozonolyzed to give an aldehyde (5) which was condensed with phosphatidyl-ethanolamine (PE) in the presence of sodium cyanoborohydride to afford CI-22 (6). In this reductive amination, the reaction mixture of the aldehyde (5) and phosphatidylethanolamine should be heated first at 70°C for 2 h followed by the addition of a reducing reagent (24).…”

Section: Synthesis Of the Ganglioside Gd3 Mimetics Ci-22 And Tms-42mentioning

confidence: 99%

Ganglioside GD3 and Its Mimetics Induce Cytochrome c Release from Mitochondria

Inoki

Miura

Kajimoto

et al. 2000

Biochemical and Biophysical Research Communications

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“…The mass spectrometric results were corroborated by TLC immunostaining and ELISA, showing that the antibodies react with neoglycolipids derived from the glycans of AMOG, RNase B and from oligomannosidic glycans of defined structures, but not with neoglycolipids containing other neutral glycans. Obviously, both antibodies do not require the intact di-//-acetylglucosamine unit for recognition because the terminal //-acetylglucosamine residue is cleaved by endoglycosidase H treatment and the A'-acetylglucosamine residue linked /31-4 to the mannotriose core is modified during the derivatization of oligosaccharides to neoglycolipids (Tang et al, 1985). The binding of the L3 and L4 antibodies to neoglycolipid containing defined oligomannosidic glycans increased from Mang-to Mans-neoglycolipid, i.e.…”

Section: Discussionmentioning

confidence: 99%

Monoclonal antibodies raised against membrane glycoproteins from mouse brain recognize N-linked oligomannosidic glycans

Schmitz¹,

Peter‐Katalinić²,

Egge³

et al. 1993

Glycobiology

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Monoclonal L3 and L4 antibodies have been shown to recognize carbohydrate epitopes on several neural cell adhesion molecules; these epitopes can be released by treatment with endoglycosidase H. In the present study, we have identified the oligosaccharides released by endoglycosidase H from the cell adhesion molecules AMOG and LI by fast-atom bombardment mass spectrometry as being solely of the oligomannosidic type. Using neoglycolipids of oligomannosidk glycans, we also report that both antibodies show the highest reactivity with the a-manno-pentaose Manal-3-[Manal-6(Manal-3)Manal-6]-Man, but decreasing reactivity with the a-manno-hexaose, heptaose, octaose and nonaose glycans. Thus, to our knowledge, we describe here for the first time monoclonal antibodies recognizing A L glycosidical]y linked oligomannosidic glycans.

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Novel approach to the study of the antigenicities and receptor functions of carbohydrate chains of glycoproteins

Cited by 125 publications

References 37 publications

Advances on the compositional analysis of glycosphingolipids combining thin-layer chromatography with mass spectrometry

Advances on the compositional analysis of glycosphingolipids combining thin-layer chromatography with mass spectrometry

Ganglioside GD3 and Its Mimetics Induce Cytochrome c Release from Mitochondria

Monoclonal antibodies raised against membrane glycoproteins from mouse brain recognize N-linked oligomannosidic glycans

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