A mild and efficient methodology for the rearrangement of protected asparagine and protected glutamine is reported; good results are obtained with a wide selection of protecting groups.

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http://dx.doi.org/10.1039/b801909fDOI Listing

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Peptidomimetics containing ( S)- or ( R)-imidazolidin-2-one-4-carboxylate (Imi) have been obtained by the expedient in-peptide cyclization of ( S)- or ( R)-α,β-diaminopropionic acid (Dap) residues. These Imi scaffolds behave as proline analogues characterized by a flat structure and a trans-restricted geometry of the preceding peptide bond and induce well-defined secondary structures in a biomimetic environment. While ( S)-Imi peptides adopted a γ'-turn conformation, ( R)-Imi induced the contemporary formation of a γ-turn and a rare 11-membered H-bonded structure in the 2→4 opposite direction of the sequence, identified as a ε-turn.

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A mild and efficient methodology for the rearrangement of protected asparagine and protected glutamine is reported; good results are obtained with a wide selection of protecting groups.

View Article and Find Full Text PDF

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