Strengthening the bond: The introduction of a thiol tag in combination with chemoselective ligation to form a disulfide‐linked bioconjugate is a selective and useful method for site‐selective protein glycosylation. The phosphine‐mediated desulfurization of such glycoconjugates to their reductant‐resistant thioether‐linked counterparts completes a convergent, site‐selective synthesis of thioether‐linked glycoproteins (see scheme).
[reaction: see text] Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28 simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning strategies.
A sweet solution: A strategy for the synthesis of well‐defined carbohydrate‐based vaccines is presented. The approach couples complex oligosaccharide synthesis to site‐specific conjugation methodology to provide pure glycoprotein vaccine candidates (see scheme).
Die Einführung einer Thiolgruppe in Kombination mit einer chemoselektiven Ligation unter Bildung eines Disulfid‐verbrückten Biokonjugats ist eine selektive und nützliche Methode zur ortsselektiven Proteinglycosylierung. Die Phosphan‐vermittelte Entschwefelung solcher Glycokonjugate zu reduktionsbeständigen Thioether‐verbrückten Analoga vervollständigt eine konvergente, ortsselektive Synthese Thioether‐verbrückter Glycoproteine (siehe Schema).
[reactions: see text] N-Iodosuccinimide provides a mild, convenient, and tuneable reagent for the selective mono- or didebenzylation in representative, multifunctionalized carbohydrate and amino acid derived N-dibenzylamines with neighboring O-functionality.
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