Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides

Khanh Ha, Iryna Oleksandrivna Lebedyeva, Sadra Hamedzadeh, Zhiliang Li, Ryan Quiñones, Girinath G. Pillai, Byron Williams, Amir Nasajpour, Kristin Martin, Abdullah M. Asiri, Alan R. Katritzky

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo- dimerization from readily available Cbz-dipeptidoyl benzotriazolides is reported (Cbz=carboxybenzyl).

Original languageEnglish (US)
Pages (from-to)4874-4879
Number of pages6
JournalChemistry - A European Journal
Volume20
Issue number17
DOIs
StatePublished - Apr 22 2014
Externally publishedYes

Keywords

  • benzotriazoles
  • cyclodimerization
  • lactamization
  • macrocycles
  • peptides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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  • Cite this

    Ha, K., Lebedyeva, I. O., Hamedzadeh, S., Li, Z., Quiñones, R., Pillai, G. G., Williams, B., Nasajpour, A., Martin, K., Asiri, A. M., & Katritzky, A. R. (2014). Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides. Chemistry - A European Journal, 20(17), 4874-4879. https://doi.org/10.1002/chem.201304262