Gabapentin hybrid peptides and bioconjugates

Iryna Oleksandrivna Lebedyeva, David A. Ostrov, John Neubert, Peter J. Steel, Kunal Patel, Sean M. Sileno, Kevin Goncalves, Mohamed A. Ibrahim, Khalid A. Alamry, Alan R. Katritzky

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (L-Ala-Gbp, L-Val-Gbp, L-Ala-L-Phe-Gbp, Gly-L-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.

Original languageEnglish (US)
Pages (from-to)1479-1486
Number of pages8
JournalBioorganic and Medicinal Chemistry
Volume22
Issue number4
DOIs
StatePublished - Feb 15 2014
Externally publishedYes

Keywords

  • Benzotriazole
  • Coupling
  • Cyclization
  • Gabapentin
  • Peptide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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  • Cite this

    Lebedyeva, I. O., Ostrov, D. A., Neubert, J., Steel, P. J., Patel, K., Sileno, S. M., Goncalves, K., Ibrahim, M. A., Alamry, K. A., & Katritzky, A. R. (2014). Gabapentin hybrid peptides and bioconjugates. Bioorganic and Medicinal Chemistry, 22(4), 1479-1486. https://doi.org/10.1016/j.bmc.2013.12.017