An alternative approach to the synthesis of peptides containing a cystathionine bridge

Jitendra R. Harjani, Beow Keat Yap, Raymond S. Norton, Jonathan B. Baell

Research output: Contribution to journalArticle

Abstract

A new method for the synthesis of cystathionine containing cyclic peptides has been developed. Conventionally such systems are typically made with relatively late-stage on-resin cyclisation involving reaction between a chlorohomoalanine and cysteine residue. We offer a different approach involving early incorporation of a cystathionine residue through on-resin reaction between a cysteine residue and an N-Alloc iodohomoalanine cumyl ester. Subsequent cyclisation then involves amide bond formation. The success of this method was demonstrated by applying it to the synthesis of a cystathionine analogue of the disulfide bridge cyclic peptide, N-acetylated cyclic peptide c[CVDINNNC]-NH2, a biologically active iNOS binding epitope mimetic that binds tightly to the protein, SPSB2. Our method expands the repertoire of synthetic options towards the construction of cystathionine containing cyclic peptides.

LanguageEnglish
Pages3256-3261
Number of pages6
JournalTetrahedron
Volume72
Issue number23
DOIs
StatePublished - 9 Jun 2016

Keywords

  • Cyclopeptides
  • Cystathionine
  • SPSB2-iNOS

Cite this

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An alternative approach to the synthesis of peptides containing a cystathionine bridge. / Harjani, Jitendra R.; Yap, Beow Keat; Norton, Raymond S.; Baell, Jonathan B.

In: Tetrahedron, Vol. 72, No. 23, 09.06.2016, p. 3256-3261.

Research output: Contribution to journalArticle

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