1.
Chemistry
; 15(45): 12184-8, 2009 Nov 16.
Artigo
em Inglês
| MEDLINE
| ID: mdl-19830748
2.
J Org Chem
; 73(2): 652-60, 2008 Jan 18.
Artigo
em Inglês
| MEDLINE
| ID: mdl-18076186
RESUMO
A practical synthesis of a new bifunctional diketopiperazine (DKP) scaffold 1, formally derived from the cyclization of L-aspartic acid and (S)-2,3-diaminopropionic acid, is reported. DKP-1 bears a carboxylic acid and an amino functionalities in a cis relationship, which have been used to grow peptide sequences. Tetra-, penta-, and hexapeptidomimetic sequences were prepared by solution-phase peptide synthesis (Boc strategy). Conformational analysis of these derivatives was carried out by a combination of 1H NMR spectroscopy, IR spectroscopy, CD spectroscopy, and computer modeling, and reveals the formation of beta-hairpin mimics involving 10-membered and 18-membered H-bonded rings and a reverse turn of the growing peptide chain.