Projects per year
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.
Original language | English |
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Pages (from-to) | 3256-3261 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 72 |
Issue number | 23 |
DOIs | |
Publication status | Published - 9 Jun 2016 |
Keywords
- Cyclopeptides
- Cystathionine
- SPSB2-iNOS
Projects
- 4 Finished
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Inhibitors of Inducible Nitric Oxide Synthase (iNOS) Regulation as a Basis for Novel Anti-Infective Agents
Norton, R., Scanlon, M. & Baell, J.
National Health and Medical Research Council (NHMRC) (Australia)
1/01/12 → 31/12/14
Project: Research
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NHMRC Research Fellowship
Baell, J.
National Health and Medical Research Council (NHMRC) (Australia)
1/01/12 → 31/12/16
Project: Research
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Colorectal cancer - molecular basis to targeted therapeutics
Lackmann, M., Burgess, A., Caruso, F., Ernst, M. R. W., Garrett, T., Heath, J., Ramsey, R., Scott, A. & Simpson, R. J.
National Health and Medical Research Council (NHMRC) (Australia)
1/09/09 → 31/12/13
Project: Research