Synthesis and biological activity of novel backbone-bicyclic: Substance- P analogs containing lactam and disulfide bridges

Gal Bitan, Inna Sukhotinsky, Yaffa Mashriki, Menachem Hanani, Zvi Selinger, Chaim Gilon*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

A biased library of 60 novel backbone-bicyclic Substance P analogs was prepared by the simultaneous multiple peptide synthesis method. The peptides, containing both a lactam and a disulfide ring, were synthesized by combined Boc and Fmoc chemistries, and were cyclized on the resin. Cleavage of the S- benzyl group and oxidation of the sulfhydryl groups was enabled by adaptation of the diphenylsulfoxide trichloromethylsilane method to solid-phase synthesis. The peptides were screened for NK-1 and NK-3 activity, and were found to be weak agonists.

Original languageEnglish
Pages (from-to)421-426
Number of pages6
JournalJournal of Peptide Research
Volume49
Issue number5
DOIs
StatePublished - 1997

Keywords

  • Backbone-cyclic peptides
  • Peptide libraries
  • Substance P analog

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