Bioorganic synthesis of a recombinant HIV-1 fusion inhibitor, SC35EK, with an N-terminal pyroglutamate capping group

Kazumi Kajiwara, Kentaro Watanabe, Rei Tokiwa, Tomoko Kurose, Hiroaki Ohno, Hiroko Tsutsumi, Yoji Hata, Kazuki Izumi, Eiichi Kodama, Masao Matsuoka, Shinya Oishi, Nobutaka Fujii

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The bioorganic synthesis of an end-capped anti-HIV peptide from a recombinant protein was investigated. Cyanogen bromide-mediated cleavage of two Met-Gln sites across the target anti-HIV sequence generated an HIV-1 fusion inhibitor (SC35EK) analog bearing an N-terminal pyroglutamate (pGlu) residue and a C-terminal homoserine lactone (Hsl) residue. The end-capped peptide, pGlu-SC35EK-Hsl, had similar bioactivity and biophysical properties to the parent peptide, and an improved resistance to peptidase-mediated degradation was observed compared with the non-end-capped peptide obtained using standard recombinant technology.

Original languageEnglish
Pages (from-to)7964-7970
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number23
DOIs
Publication statusPublished - 2009 Dec 1
Externally publishedYes

Keywords

  • Anti-HIV peptide
  • Fusion inhibitor
  • HIV
  • Pyroglutamate

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Bioorganic synthesis of a recombinant HIV-1 fusion inhibitor, SC35EK, with an N-terminal pyroglutamate capping group'. Together they form a unique fingerprint.

  • Cite this

    Kajiwara, K., Watanabe, K., Tokiwa, R., Kurose, T., Ohno, H., Tsutsumi, H., Hata, Y., Izumi, K., Kodama, E., Matsuoka, M., Oishi, S., & Fujii, N. (2009). Bioorganic synthesis of a recombinant HIV-1 fusion inhibitor, SC35EK, with an N-terminal pyroglutamate capping group. Bioorganic and Medicinal Chemistry, 17(23), 7964-7970. https://doi.org/10.1016/j.bmc.2009.10.017