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α-N-linked glycopeptides are unnatural molecules, sinc e they display an α-linkage between the peptide side chain and the sugar moiety, unlike nat ural N-linked glycopeptides that connect the peptide to the glycan through a β-N-glycosidic bond. This novel type of peptide glycos ylation could introduce structural modifications that can mimic a nd/or interfere with molecular recognition events. 4 Direct glycosylation of peptide chains is not viab le for the synthesis of molecules with the α-N-linked configuration, since the corresponding αlycosyl amines isomerise to the β-anomers. Only very recently N-Fmoc-protected glycosyl amino acids have been effi ci ntly and stereoselectively synthesized and linearly incorpor ated into a peptide sequence. 3

Synthesis of Unnatural Alfa-<i>N</i>-linked Glycopeptides with Potential Antifreeze Activity