6533b834fe1ef96bd129e2af
RESEARCH PRODUCT
Synthesis of enantiopure pyrrolidine-derived peptidomimetics and oligo-beta-peptides via nucleophilic ring-opening of beta-lactams.
Eduardo AlonsoCarlos Del PozoAlberto MacíasJavier GonzalezAntonio Morán Ramallalsubject
Models MolecularMagnetic Resonance SpectroscopyPyrrolidinesPeptidomimeticStereochemistryStereoisomerismRing (chemistry)beta-LactamsChemical synthesisPyrrolidinechemistry.chemical_compoundNucleophileβ lactamschemistry.chemical_classificationOrganic ChemistryMolecular MimicryStereoisomerismNuclear magnetic resonance spectroscopyGeneral MedicineMSH Release-Inhibiting HormoneAmino acidEnantiopure drugchemistryDrug DesignLactamOligopeptidesdescription
The synthesis of the two enantiomers of pyrrolidine-derived spiro beta-lactams by resolution with D- and L-Boc phenylalanine is described. The potential of these optically active spiro beta-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 beta-lactams have shown their utility in the preparation of beta-peptides. As an example, a homo-tetra-beta-peptide was synthesized. This research will continue in the future in order to obtain higher peptides with potential biological activity.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-09-26 | The Journal of organic chemistry |