Preparation of peptide thioesters through fmoc-based solid-phase peptide synthesis by using amino thioesters

Research output: Contribution to journalJournal articleResearchpeer-review

N. Stuhr-Hansen, T.S. Wilbek, K. Strømgaard

An effective procedure for the synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis was developed. The free C terminus of a fully protected peptide was coupled in solution with the free amino group of an amino thioester. This furnished the fully protected peptide thioester, which was globally deprotected to afford the desired unprotected peptide thioester. The method is compatible with labile groups such as phosphoryl and glycosyl moieties. The synthesis of peptide alkyl thioesters by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis (SPPS) is developed. The free C terminus of a fully protected peptide is coupled in solution with the free amino group of an amino thioester. This furnishes the fully protected peptide thioester, which can be globally deprotected to afford the desired unprotected peptide thioester.
Original languageEnglish
JournalEuropean Journal of Organic Chemistry
Volume2013
Issue number24
Pages (from-to)5290-5294
Number of pages5
ISSN1434-193X
DOIs
Publication statusPublished - 1 Aug 2013

ID: 96081956