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Published December 2, 2000 | public
Journal Article

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

Abstract

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.

Additional Information

© 2000 Elsevier Science Ltd. Received 31 August 2000; revised 12 September 2000; accepted 14 September 2000. We are grateful to the National Institutes of Health for support of this work (GM-27681) and a National Research Service Award to A.K.M.

Additional details

Created:
August 19, 2023
Modified:
October 18, 2023