914389-51-8Relevant articles and documents
Synthesis of enantiopure pyrrolidine-derived peptidomimetics and oligo-β-peptides via nucleophilic ring-opening of β-lactams
Macias, Alberto,Ramallal, Antonio Moran,Alonso, Eduardo,Del Pozo, Carlos,Gonzalez, Javier
, p. 7721 - 7730 (2007/10/03)
(Chemical Equation Presented) The synthesis of the two enantiomers of pyrrolidine-derived spiro β-lactams by resolution with D- and L-Boc phenylalanine is described. The potential of these optically active spiro β-lactams on the synthesis of peptidomimetics as analogues of melanostatin is evaluated. Theoretical studies of several models, at the Becke3LYP/6-31+G* level of theory, together with previous experimental evidences from our group, gathered by NMR, allow us to design structures that can efficiently mimic some biologically active peptide-type molecules. On the other hand, the spiro β-lactams have shown their utility in the preparation of β-peptides. As an example, a homo-tetra-β-peptide was synthesized. This research will continue in the future in order to obtain higher peptides with potential biological activity.