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 alky
lation with benzyl bromide to produce the target thioesters in good yield.
The thioesters thus prepared were conjugated to peptides to produce polyami
de-peptide chimeras using the 'native chemical ligation' method. This flexi
ble synthetic procedure provides a ready route to both natural and unnatura
l substrates for chemical ligation reactions. (C) 2000 Elsevier Science Ltd
. All rights reserved.