An Efficient Convergent Synthesis of GP1c Ganglioside Epitope

Tanaka, Hiroshi; Nishiura, Yuji; Takahashi, Takashi

doi:10.1021/ja807482t

Cited by 64 publications

(35 citation statements)

References 7 publications

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“…Some of these sialyl donors have been applied in the synthesis of α2–8-linked disialylated oligosaccharides in moderate yields 40b,42b,44. The 1,5-lactam derivative of sialic acids45 and 5- N ,4- O -carbonyl protected oxazolidinone sialyl donor46 have also been developed for the synthesis of α2–8-linked disialosides. Despite the advance, current chemical synthesis of sialosides remains to be a time-consuming process and requires skillful expertise.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of GD3 Oligosaccharides and Other Disialyl Glycans Containing Natural and Non-natural Sialic Acids

et al. 2009

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In order to understand the biological importance of naturally occurring sialic acid variations on disialyl structures in nature, we developed an efficient two-step multi-enzyme approach for the synthesis of a series of GD3 ganglioside oligosaccharides and other disialyl glycans containing a terminal Siaα2–8Sia component with different natural and non-natural sialic acids. In the first step, α2–3- or α2–6-linked monosialylated oligosaccharides were obtained using a one-pot three-enzyme approach. These compounds were then used as acceptors for the α2–8-sialyltransferase activity of a recombinant truncated multi-functional Campylobacter jejuni sialyltransferase CstII mutant, CstIIΔ32I53S, to produce disialyl oligosaccharides. The α2–8-sialyltransferase activity of CstIIΔ32I53S has promiscuous donor substrate specificity and can tolerate various substitutions at C-5 or C-9 of the sialic acid in CMP-sialic acid, while its acceptor substrate specificity is relatively restricted. The terminal sialic acid residues in the acceptable monosialylated oligosaccharide acceptors are restricted to Neu5Ac, Neu5Gc, KDN, and some of their C-9 modified forms but not their C-5 derivatives. The disialyl oligosaccharides obtained are valuable probes for their biological studies.

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Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Synthesis of GD3 Oligosaccharides and Other Disialyl Glycans Containing Natural and Non-natural Sialic Acids

et al. 2009

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“…[111] 2006 berichteten Takahashi und Mitarbeiter erstmals über den Ein- Ganglioside aus der C-Reihe ist. [112] Kurz nach Takahashis bahnbrechender Entdeckung führten Crich und Mitarbeiter eine N-acetylierte Variante 103 ein (Abbildung 8).…”

Section: 5-oxazolidinon-geschützte Sialyldonoren Für Effiziente Synunclassified

Auf dem Weg zur automatisierten Oligosaccharid‐ Synthese

Hsu

Hung

et al. 2011

Angewandte Chemie

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Kohlenhydrate spielen eine wichtige Rolle bei biologischen Vorgängen. Das Fortschrittstempo der Kohlenhydratforschung ist jedoch relativ langsam, was unter anderem mit der Komplexität der Kohlenhydratstrukturen und dem Fehlen allgemein anwendbarer Synthesemethoden und Verfahren zur Untersuchung dieser Klasse von Biomolekülen zusammenhängt. Jüngste Fortschritte in der Synthese haben ergeben, dass viele dieser Probleme umgangen werden können. In diesem Aufsatz beschreiben wir die Methoden, die entwickelt wurden, um mit den Herausforderungen kohlenhydratvermittelter biologischer Vorgänge umzugehen. Besonderes Augenmerk wird dabei auf die Entwicklung der automatisierten Synthese von Oligosacchariden gerichtet. Darüber hinaus werden auch Kohlenhydrat‐Mikroarrays und Impfstoffe auf Kohlenhydratbasis behandelt.

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“…With the C6-OH galactose acceptor, the building blocks provide excellent α-selectivity without the nitrite effect (38,39 (35). They also synthesized ganglioside GP1c having oligosialic acid branches at non-reducing terminus of the glycan chain (40). Synthesis of α(2,9)-oligosialic acid came from using either a linear strategy for tetramer or a onepot glycosylation strategy with resin-capture purifications using the combination of S-benzoxazolyl (SBox) and SEt leaving groups for the trimer ( Our group modified the 4,5-oxazolidinone locked sialic acid building blocks by appending further ring-fixing protection using cyclic silylene at the 5,7-positions.…”

Section: 5-oxazolidinone Building Blocks For Oligosialic Acid Symentioning

confidence: 99%

Recent Strategies for Stereoselective Sialylation and Their Application to the Synthesis of Oligosialosides

Hanashima

2011

TIGG

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S i a l i c a c i d s o n t h e n o n -r e d u c i n g t e r m i n u s o f sialylgylcans are abundantly expressed on the surface of mammalian cells. They play vital roles in cell-cell interactions and during infection by pathogenic bacteria and viruses. The chemical synthesis of sialylated glycans has been investigated for more than two decades, and interesting chemistry has been developed for coupling of sialic acid in an α-selective manner. Chemoenzymatic approaches are also now available for stereoselective sialylations. This mini-review focuses on very recent advances in stereoselective chemical sialylations and synthesis of natural sialylglycans using novel strategies, especially for the synthesis of the oligo/polysialic acid structure.

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An Efficient Convergent Synthesis of GP1c Ganglioside Epitope

Cited by 64 publications

References 7 publications

Chemoenzymatic Synthesis of GD3 Oligosaccharides and Other Disialyl Glycans Containing Natural and Non-natural Sialic Acids

Chemoenzymatic Synthesis of GD3 Oligosaccharides and Other Disialyl Glycans Containing Natural and Non-natural Sialic Acids

Auf dem Weg zur automatisierten Oligosaccharid‐ Synthese

Recent Strategies for Stereoselective Sialylation and Their Application to the Synthesis of Oligosialosides

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