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Article
GM1 structural requirements to mediate neuronal functions
Since the 1980s, it has been known that the administration of ganglioside GM1 to cultured cells induced or enhanced neuronal differentiation. GM1 mechanism of action relies on its direct interaction and subseq...
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Article
Fluorescent GD2 analog for single-molecule imaging
Ganglioside GD2 is associated with the proliferation and migration of breast cancer cells. However, the precise role of GD2 is unclear because its tendency to form dynamic and transient domains in cell plasma ...
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Article
Improved synthesis of CD22-binding sialosides and its application for further development of potent CD22 inhibitors
CD22, one of the sialic acid-binding immunoglobulin-like lectins (Siglecs), regulates B lymphocyte signaling via its interaction with glycan ligands bearing the sequence Neu5Ac/Gcα(2→6)Gal. We have developed t...
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Protocol
Chemical Synthesis of Gangliosides
Synthetic methodologies for gangliosides have evolved over the past three decades. The strategies for constructing ganglioside skeletons can generally be classified as late-stage ceramide coupling, the glucosy...
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Chapter
Chemical and Enzymatic Synthesis and Production of Glycans
Oligosaccharide, Glycoconjugates, Glycosylation, Stereoselectivity
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Article
Raft-based interactions of gangliosides with a GPI-anchored receptor
Monitoring new fluorescent ganglioside analogs at a single-molecule level suggests that gangliosides associate dynamically with GPI-anchored protein monomers, transient homodimer rafts, and clustered signaling...
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Reference Work Entry In depth
Gangliosides Synthesis
Various methodologies for the chemical synthesis of gangliosides have been explored so far and a lot of natural gangliosides including their structural analogues have been synthesized during the past three dec...
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Living Reference Work Entry In depth
Ganglioside Synthesis
Various methodologies for the chemical synthesis of gangliosides have been explored so far and a lot of natural gangliosides including their structural analogues have been synthesized during the past three dec...
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Article
Use of structure-based virtual screening in the investigation of novel human sialidase inhibitors
Recent studies have determined the molecular mechanisms underlying the pathological alterations of sialic acid or its conjugates in various human disease states, and the sialic acid modifying enzyme sialidase ...
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Article
Di-tert-butylsilylene-directed α-selective synthesis of p-nitrophenyl T-antigen analogues
Seven analogues of p-nitrophenyl T-antigen [Galβ(1→3)GalNAcα(1→O)PNP] have been synthesized as potential substrates for elucidation of the substrate specificity of endo-α-N-acetylgalactosaminidase. These compound...
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Article
Open AccessAb initio fragment molecular orbital studies of influenza virus hemagglutinin–sialosaccharide complexes toward chemical clarification about the virus host range determination
If we predict the host range of new or mutant influenza virus in advance, we are able to measure against pandemic human influenza immediately after the new virus emerges somewhere. Influenza viral hemagglutini...
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Article
Design and efficient synthesis of novel GM2 analogues with respect to the elucidation of the function of GM2 activator
To elucidate the mechanism underlying the hydrolysis of the GalNAcβ1→4Gal linkage in ganglioside GM2 [GalNAcβ1→4(NeuAcα2→3)Galβ1→4Glcβ1→1′ Cer] by β-hexosaminidase A (Hex A) with GM2 activator protein, we desi...
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Article
A highly efficient construction of GM1 epitope tetrasaccharide and its conjugation with KLH
GM1 epitope tetrasaccharide was synthesized by a condensation of sialyl-α(2–3)-gal acceptor and gal-β(1–3)-GalN donor in a highly efficient manner. After introduction of mercaptohexanol to the tetrasaccharide,...
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Article
Design and synthesis of versatile ganglioside probes for carbohydrate microarrays
A series of ganglioside GM1-, GM2-, and GM3-type probes, in which the ceramide portion is replaced with a glucose residue, were systematically synthesized based on a convergent synthetic method.
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Chapter
Synthesis of Glycolipid and Its Application
Glycolipids constitute a group of bio-active glycoconjugates along with glycoproteins and proteoglycans. The synthesis of glycolipids by chemical methods is the most reliable procedure because of microheteroge...
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Article
A chemical synthesis of UDP-LacNAc and its regioisomer for finding ‘oligosaccharide transferases’
A chemical synthesis of uridine 5’-diphospho-N-acetyllactosamine (Galβ(1→4)GlcNAc-UDP; UDP-LacNAc) and Galβ(1→3)GlcNAc-UDP is described. Coupling of the disaccharide imidate derivatives with dibenzylphosphate gav...
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Article
Synthesis and enzymatic susceptibility of a series of novel GM2 analogs
A series of GM2 analogs in which GM2 epitope was coupled to a variety of glycosyl lipids were designed and synthesized to investigate the mechanism of enzymatic hydrolysis of GM2 ganglioside. The coupling of N-Tr...
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Article
6-O-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid: Synthesis and antigenic reactivity against G159 monoclonal antibody
Synthesis and antigenic reactivity of 6-O-sulfo sialylparagloboside (SPG) and sialyl Lewis X (sLe X ) neo-glycolipids containing lactamized neuraminic acid are described. The sui...
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Article
Total synthesis of a cholinergic neuron-specific ganglioside GT1aα: A high affinity ligand for myelin-associated glycoprotein (MAG)
An efficient total synthesis of a cholinergic neuron-specific ganglioside GT1aα (IV3NeuAcIII6NeuAcII3NeuAc-GgOse4Cer) is described. The suitably protected sialyl-α(2→6)-gangliotriose (III6NeuAc-GgOse3) derivative...
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Article
The Structural Basis for the Susceptibility of Gangliosides to Enzymatic Degradation
The conformational properties of GM2, GalNacβ-4(Neu5Acα-3) Galβ-4Glcβ-1Cer have been compared to those of 6′-GM2, in which the linkage between the GalNAc and Gal was altered from GalNacβ-4Galβ- to GalNacβ-6Gal...
