Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters

Jesper Brask, F. Albericio, Knud Jørgen Jensen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalORGANIC LETTERS
Volume5
Issue number16
Pages (from-to)2951-2953
ISSN1523-7060
Publication statusPublished - 2003

Fingerprint Dive into the research topics of 'Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters'. Together they form a unique fingerprint.

Cite this