Use of model peptide reactions for the characterization of kinetically controlled ligation

Joongoo Lee, Yoonjin Kwon, Brad L. Pentelute, Duhee Bang

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Since the introduction of kinetically controlled ligation (KCL), a chemoselective reaction between a peptide- αthioarylester and a Cys-peptide- αthioalkylester, KCL has been utilized for the total chemical synthesis of large proteins (i.e., lysozyme and HIV-protease) by providing fully convergent synthetic routes. Although KCL has the potential to become an important chemistry for protein synthesis, the principle of KCL is not fully characterized. In particular, prior work on KCL has focused on the reactivity difference of the two different - αthioester forms-alkyl vs aryl. Another equally important feature of KCL, Xaa-Cys ligation sites, has not been investigated. The work reported here describes combinatorial KCL reactions using model peptides to dissect the interplay of the Xaa 1, Xaa 2, - αthioarylester, and - αthioalkylester. Results from these studies provide fundamental insights into the KCL reaction, and will lead to the optimal synthetic route for the routine chemical synthesis of large target protein molecules.

Original languageEnglish
Pages (from-to)1645-1649
Number of pages5
JournalBioconjugate Chemistry
Volume22
Issue number8
DOIs
Publication statusPublished - 2011 Aug 17

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Bioengineering
  • Biomedical Engineering
  • Pharmacology
  • Pharmaceutical Science
  • Organic Chemistry

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