Automated synthesis of lipomannan backbone α(1-6) oligomannoside via glycosyl phosphates: glycosyl tricyclic orthoesters revisited

Liu, Xinyu; Wada, Reiko; Boonyarattanakalin, Siwarutt; Castagner, Bastien; Seeberger, Peter H.

doi:10.1039/b804069a

Cited by 27 publications

(21 citation statements)

References 24 publications

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“…α-Xylosyl bromides that contain an ester protective group at C2, such as acetate, benzoate, or pivaloate, are reacted with a base and an alcohol or thiol to form a bicyclic orthoester over O1 and O2 (Scheme 12). 142,216,[274][275][276][277][278][279][280] Instead of reacting the orthoester with an alcohol to form a β-xyloside, treatment with acid generates a tricyclic orthoester also involving O4, where position 3 can be selectively modified.…”

Section: Orthoestersmentioning

confidence: 99%

Chemistry of xylopyranosides

Thorsheim

Siegbahn

Johnsson

et al. 2015

Carbohydrate Research

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Xylose is one of the few monosaccharidic building blocks that are used by mammalian cells. In comparison with other monosaccharides, xylose is rather unusual and, so far, only found in two different mammalian structures, i.e. in the Notch receptor and as the linker between protein and glycosaminoglycan (GAG) chains in proteoglycans. Interestingly, simple soluble xylopyranosides can not only initiate the biosynthesis of soluble GAG chains but also function as inhibitors of important enzymes in the biosynthesis of proteoglycans. Furthermore, xylose is a major constituent of hemicellulosic xylans and thus one of the most abundant carbohydrates on Earth. Altogether, this has spurred a strong interest in xylose chemistry. The scope of this review is to describe synthesis of xylopyranosyl donors, as well as protective group chemistry, modifications, and conformational analysis of xylose.

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Section: Orthoestersmentioning

confidence: 99%

Chemistry of xylopyranosides

Thorsheim

Siegbahn

Johnsson

et al. 2015

Carbohydrate Research

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“…[124] Die allgemeine Anwendbarkeit der automatisierten SPOS wurde an der Synthese eines Nonasaccharids, des Le yLe x (KH-1)-Antigenderivats 124 gezeigt (Schema 24). [125] Die Glycosylphosphate [126] Mit der automatisierten Oligosaccharidsynthese wurden verschiedene wichtige Kohlenhydrate synthetisiert, darunter das Globo-H-Hexasaccharid 133 (Schema 25), [128] das Kernpentasaccharid N-verknüpfter Glycane, [129] b-Mannosid, [130] Oligomannoside, [131] Oligorhamnoside, [132] die PhytoalexinElicitorfamilie aus Glucan [124a] und die parasitischen Impfstoffkandidaten gegen Malaria und Leishmaniose (siehe Abschnitt 7).…”

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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“…Although a large excess of sugar donors are still required, great advances have been achieved recently as demonstrated in the synthesis of lipomannan backbone α1,6-hexamannoside 26 (Figure 3A) [29], tumor-associated carbohydrate antigens Gb-3 and Globo-H [30], and oligoglucosamines [31]. …”

Section: Chemical Synthesis Of Oligosaccharidesmentioning

confidence: 99%

“…Automated synthesis of A) hexamannoside 26 [29] and B) branched pentasaccharide 30 [32••]. (a) TMSOTf, CH 2 Cl 2 , 5 °C, 30 min; (b) TBAF, THF, rt, 5h; (c) 1 M NH 2 NH 2 , Pyr., AcOH, rt, 30 min.…”

Section: Figurementioning

confidence: 99%

Recent progress in chemical and chemoenzymatic synthesis of carbohydrates

Muthana

Cao

Chen

2009

Current Opinion in Chemical Biology

125

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Summary The important roles that carbohydrates play in biological processes and their potential application in diagnosis, therapeutics, and vaccine development have made them attractive synthetic targets. Despite ongoing challenges, tremendous progresses have been made in recent years for the synthesis of carbohydrates. The chemical glycosylation methods have become more sophisticated and the synthesis of oligosaccharides has become more predictable. Simplified one-pot glycosylation strategy and automated synthesis are increasingly used to obtain biologically important glycans. On the other hand, chemoenzymatic synthesis continues to be a powerful alternative for obtaining complex carbohydrates. This review highlights recent progress in chemical and chemoenzymatic synthesis of carbohydrates with a particular focus on the methods developed for the synthesis of oligosaccharides, polysaccharides, glycolipids, and glycosylated natural products.

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Automated synthesis of lipomannan backbone α(1-6) oligomannoside via glycosyl phosphates: glycosyl tricyclic orthoesters revisited

Abstract: Glycosyl tricyclic orthoesters provide a versatile basis for the efficient generation of glycosyl phosphates, which are used in the automated synthesis of lipomannan backbone alpha(1-6) hexa-mannoside.

Cited by 27 publications

References 24 publications

Chemistry of xylopyranosides

Chemistry of xylopyranosides

Auf dem Weg zur automatisierten Oligosaccharid‐ Synthese

Recent progress in chemical and chemoenzymatic synthesis of carbohydrates

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