A convergent synthesis of homogeneous reducible polypeptides

Mark D. Ericson, Kevin G. Rice

Research output: Contribution to journalArticle

3 Scopus citations

Abstract

The convergent syntheses of homogeneous disulfide cross-linked polypeptides are reported. Reducible polypeptides were synthesized containing four and eight dodecapeptides in two and three linear conjugation steps. Critical for the convergent methodology was the use of orthogonally protected cysteines as either acetamidomethyl (Acm) or Fmoc-thiazolidine (Thz). Both groups could be selectively deprotected with silver trifluoromethanesulfonate in the presence of internal disulfide bonds using TFA and aqueous conditions, respectively. This approach allows for large, reducible polypeptides to be synthesized in efficient yields and minimizes the number of conjugation steps, allowing the development and optimization of gene delivery polypeptides containing multiple peptide components necessary to overcome the numerous in vivo barriers for efficacious gene delivery.

Original languageEnglish (US)
Pages (from-to)4746-4748
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number35
DOIs
StatePublished - Aug 28 2013
Externally publishedYes

Keywords

  • Acetamidomethyl
  • Convergent synthesis
  • Cysteine
  • Reducible polypeptides
  • Thiazolidine

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