N-Dmc protected amino acid aglycones: versatile hydrogenolysis stable acceptors for O-glycosylation |
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Authors: | Barrie Kellam Paul A Ward Aisyah S Abdul Rahim Siri Ram Chhabra |
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Institution: | School of Pharmacy, Centre for Biomolecular Sciences, University of Nottingham, University Park, Nottingham NG7 2RD, UK |
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Abstract: | Nα-(4,4-Dimethyl-2,6-dioxocyclohexylidenemethylene) (Dmc) protected l-serine, l-threonine and l-homoserine have been prepared as tert-butyl esters in excellent yields. These hydrogenolysis stable acceptors underwent efficient α-O-glycosylation with an l-fucopyranosyl bromide donor and also allowed convenient protecting group manipulations to ultimately deliver novel glycoamino acid building blocks suitable for Fmoc based solid-phase glycopeptide synthesis. |
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Keywords: | Protecting groups Glycosylation Amino acids and derivatives |
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