Pyrrolidinone-modified di- and tripeptides: highly diastereoselective preparation and investigation of their stability

Masood Hosseini, David Ackland Tanner, A. Murray, Janne Ejrnæs Tønder

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Volume5
Issue number21
Pages (from-to)3486-3494
ISSN1477-0520
DOIs
Publication statusPublished - 2007

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