Iterative reducible ligation to form homogeneous penicillamine cross-linked polypeptides

Mark D. Ericson, Kevin G. Rice

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

The syntheses of homogeneous penicillamine disulfide cross-linked polypeptides are reported. Dodecapeptides containing N-terminal, C-terminal, or N- and C-terminal Pen were serially ligated into 36 amino acid polypeptides linked through Cys-Pen, Pen-Cys, or Pen-Pen disulfide bonds. Critical to the syntheses was the incorporation of thiazolidine masked Cys and Pen as the N-terminal residues and selective hydrolysis with silver trifluoromethanesulfonate in acidic aqueous conditions to generate a free thiol for subsequent ligation. This approach allows the synthesis of homogeneous disulfide cross-linked polypeptides that have different reductive stabilities and have application in gene delivery by undergoing a tempered reductive triggered release of DNA.

Original languageEnglish (US)
Pages (from-to)3440-3443
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number26
DOIs
StatePublished - Jun 26 2013
Externally publishedYes

Keywords

  • Gene delivery
  • Penicillamine
  • Reducible polypeptides
  • Thiazolidine

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