TY - JOUR
T1 - Pyrrolidinone-modified di- and tripeptides: highly diastereoselective preparation and investigation of their stability
AU - Hosseini, Masood
AU - Tanner, David Ackland
AU - Murray, A.
AU - Tønder, Janne Ejrnæs
PY - 2007
Y1 - 2007
N2 - Pyrrolidine-2,4-diones have been identified as a novel starting point for the synthesis of peptide analogues. This paper describes a method for the efficient and diastereoselective incorporation of this moiety into peptide chains to furnish di- and tripeptide analogs. The stability of these pyrrolidinone modified di- and tripeptides was found to be markedly improved when compared to that of a natural peptide. In addition, solid phase peptide synthesis employing a pyrrolidinone containing tripeptide is demonstrated.
AB - Pyrrolidine-2,4-diones have been identified as a novel starting point for the synthesis of peptide analogues. This paper describes a method for the efficient and diastereoselective incorporation of this moiety into peptide chains to furnish di- and tripeptide analogs. The stability of these pyrrolidinone modified di- and tripeptides was found to be markedly improved when compared to that of a natural peptide. In addition, solid phase peptide synthesis employing a pyrrolidinone containing tripeptide is demonstrated.
U2 - 10.1002/chin.200812204
DO - 10.1002/chin.200812204
M3 - Journal article
SN - 1477-0520
VL - 5
SP - 3486
EP - 3494
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
IS - 21
ER -