engleski

N‐Alkylated C‐Glycosyl Amino Acid Derivatives: Synthesis by a One‐Pot Four‐Component Ugi Reaction

C-glycosides represent an important group of naturally occurring glycosylation derivatives but also efficient mimetics of native O- glycosides. We describe here a one-pot four- component methodology toward a library of N- alkylated C-glycosyl amino acid derivatives comprising seven different isopropylidene- protected carbohydrate units. The applied methodology tolerates different amines and isocyanides and provides access to Ugi products in yields up to 85 %. X-ray analysis of selected products bearing three different carbohydrate motifs and comparison of their crystal structures with similar ones deposited in Cambridge Crystallographic Database revealed that four structures adopt different conformations, mostly not typical for peptide structures. This property opens the possibility to exploit here described N-alkylated C- glycosyl amino acid derivatives as templates for accessing different biotic and abiotic secondary structures.

amino acids ; carbohydrates ; C-glycosides ; peptidomimetics ; Ugi reaction

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