Preparation of thioesters for the ligation of peptides with non-native substrates

✍ Scribed by Anna K Mapp; Peter B Dervan

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 72 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)01600-2

✦ Synopsis

A one-pot procedure for the synthesis of thioesters from primary amines is reported. Polyamides containing one or more primary amines were prepared by solid-phase synthesis and reacted with thiolane-2,5-dione followed by alkylation with benzyl bromide to produce the target thioesters in good yield. The thioesters thus prepared were conjugated to peptides to produce polyamide-peptide chimeras using the 'native chemical ligation' method. This flexible synthetic procedure provides a ready route to both natural and unnatural substrates for chemical ligation reactions.