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Royal Society of Chemistry (RSC) RSC Chemical Biology 6(6)
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    초록·키워드

    Protein glycosylation is one of the most abundant and complex post-translational modifications, necessitating many different approaches to fully understand the biological effects. Investigation using synthetic glycopeptides is limited by the high cost of building blocks; typically >100<i>x</i> more than other modified amino acids <i>e.g.</i> phosphorylation. We report a simple, low cost route to <i>O</i>-glycosylated amino acids suitable for Fmoc-SPPS in two or three steps starting from peracetylated sugars. One set of reagents can furnish either the α- or β-anomer through adjusting the equivalents and reaction time. Depending on the derivative, the cost of our route is 25-60× less than commercial alternatives and offers scope for producing modified analogues. Overall, this is a convenient and user-friendly approach to access <i>O</i>-glycosylated amino acids, urgently required for continued investigation of the manifold roles of glycosylation in biology.

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