Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry

Lee, Jun Young; Yang, Sung‐Hyun; Williams, Geoffrey M.; Brimble, Margaret A.

doi:10.1021/jo3013435

Cited by 32 publications

(12 citation statements)

References 67 publications

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“…Click chemistry has been applied to access glycopeptides [18,19] and glycoproteins, [20] though all of the reported procedures require multiple-step manipulations of the carbohydrate component. As further exemplification, this approach was applied to the direct synthesis of glycopeptides.…”

Section: Methodsmentioning

confidence: 99%

Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

et al. 2014

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The conversion of sugars into glycomimetics typically involves multiple protecting-group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high-yielding and stereoselective process is highly desirable. The combined use of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate and the Cu-catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one-step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole-linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one-pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains.

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Section: Methodsmentioning

confidence: 99%

Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

et al. 2014

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“…Acid–base extraction and purification by flash chromatography gave the novel carbohydrate building block 1 in 31% overall yield (Scheme 2). Similar carbohydrates have been used for the preparation of glycoclusters for lectin binding [25–28] and as scaffold carriers of multiple peptide antigens [17,29]. However, the synthesis of the new carbohydrate building block 1 reported here is concise and efficient, involving only one chromatographic step and takes advantage of the highly efficient “click” reaction.…”

Section: Resultsmentioning

confidence: 99%

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

Fagan¹,

Tóth²,

Simerská³

2014

Beilstein J. Org. Chem.

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SummaryA novel convergent synthetic strategy for the construction of multicomponent self-adjuvanting lipopeptide vaccines was developed. A tetraalkyne-functionalized glucose derivative and lipidated Fmoc-lysine were prepared by novel efficient and convenient syntheses. The carbohydrate building block was coupled to the self-adjuvanting lipidic moiety (three lipidated Fmoc-lysines) on solid support. Four copies of a group A streptococcal B cell epitope (J8) were then conjugated to the glyco-lipopeptide using a copper-catalyzed cycloaddition reaction. The approach was elaborated by the preparation of a second vaccine candidate which incorporated an additional promiscuous T-helper epitope.

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“…Click chemistry has been applied to access glycopeptides18, 19 and glycoproteins,20 though all of the reported procedures require multiple‐step manipulations of the carbohydrate component. As further exemplification, this approach was applied to the direct synthesis of glycopeptides.…”

Section: Methodsmentioning

confidence: 99%

Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

Lim¹,

Brimble²,

Kowalczyk³

et al. 2014

Angewandte Chemie

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The conversion of sugars into glycomimetics typically involves multiple protecting‐group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high‐yielding and stereoselective process is highly desirable. The combined use of 2‐azido‐1,3‐dimethylimidazolinium hexafluorophosphate and the Cu‐catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one‐step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole‐linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one‐pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains.

show abstract

Synthesis of Multivalent Neoglyconjugates of MUC1 by the Conjugation of Carbohydrate-Centered, Triazole-Linked Glycoclusters to MUC1 Peptides Using Click Chemistry

Cited by 32 publications

References 67 publications

Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars

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