Synthesis of divalent glycoamino acids with bis-triazole linkage

• Synthesis of bis triazole-linked divalent glycoconjugates.
• Nitro- and cyano-functionalized dialkyne building blocks as precursors of α- and β-amino acids, respectively.
• Triazole- and triazole amide-linked divalent glycoconjugates synthesized existed as rotamers.

Triazole-linked diversely functionalized divalent glycoconjugates were synthesized using Cu(I) catalyzed [3+2] cycloaddition reaction of the desired azides and alkynes. A series of per-O-acetylated glycopyranosyl azides and per-O-acetylated glucopyranosyl azidoacetamide were reacted with nitro- and cyano-functionalized dialkyne building blocks as precursors of α- and β-amino acids, respectively. To introduce more conformational flexibility in the divalent molecules, peptoid-based triazole-linked divalent glycoconjugate was also synthesized.

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