| Abstract | A fully automated solid-phase synthesis of C-neoglycopeptides has been developed using a convergent strategy. In this approach, C-glycoside derivatives (3 and 4) were coupled to resin-bound peptides using a peptide synthesizer. An advantage of the convergent approach is the ability to introduce multiple glycoside units late in the synthesis. The approach presented is highly versatile and efficient and could be used for building C-neoglycopeptide libraries. In our study, neoglycopeptides 5 and 6 were obtained from the coupling of C-glycoside derivatives (3 and 4) to a free amino group of the side chain of short peptides (2, n = 1 and 3). A similar approach was developed for the synthesis of bivalent neoglycopeptides 8 and 9 in an automated manner. The successful syntheses of C-neoglycopeptides 5, 6, 8, and 9 are the first examples of coupling of C-glycosyl carboxyl derivatives to the amino groups of the side chains of resin-bound peptides. |
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