C-terminal modified peptides
solid-phase peptide synthesis
Springer Online Journal Archives 1860-2000
Chemistry and Pharmacology
Abstract This paper describes a practical new use of3-mercaptopropionic acid as a highly versatilemultidetachable linker for solid-phase synthesis. Ourapproach is based on the stability of thealkylthioester functionality to optimized Boc-SPPSprotocols and HF treatment, as well as on the mildactivation of the thioester functionality towardnucleophilic or reductive displacement. This allowsseveral C-terminal modifications to be introduced intoa synthetic molecule during the cleavage step. We haveshown that unprotected peptides can be efficientlycleaved from a propyl thioester-polyethyleneglycol-poly-(N,N-dimethylacrylamide) copolymerresin using a great variety of nucleophiles to givethe corresponding C-terminally modified peptides(esters, thioesters, carboxylic acids, thioacids,amides, hydroxamic acids, hydrazides, alcohols). Thenucleophilic cleavage reaction is both rapid andexceptionally clean in all the cases tested.
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