Journal
ORGANIC LETTERS
Volume 5, Issue 16, Pages 2951-2953Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0351044
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Total chemical synthesis of proteins by chemoselective ligation relies on C-terminal peptide thioesters as building blocks. Their preparation by standard Fmoc solid-phase peptide synthesis is made difficult by the lability of thioesters to aminolysis by the secondary amines used for removal of the Fmoc group. Here we present a novel backbone amide linker (BAL) strategy for their synthesis in which the thioester functionality is masked as a trithioortho ester throughout the synthesis.
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