Biologically Active Cyclic Peptide Natural Products
Current efforts are being directed towards the synthesis of several complex cyclic peptide natural products. The ustiloxins & celogentins are tubulin-binding cyclic peptides that have shown potent in vitro anti-tumour activity. The echinocandins and microsclerodermins are antifungal cyclic peptides that contain several poly-hydroxylated amino acids, with several now in clinical use for the treatment of fungal infections. The general synthetic strategy involves developing methods for the stereocontrolled synthesis of the highly functionalised amino acid residues present in these peptides, followed by the development of procedures for the assembly of the amino acid components into the final cyclic peptides. We have recently prepared the dityrosine-containing cyclic peptide natural product mycocyclosin, combining our interests in dityrosine crosslinks and peptide natural products!
A. L. Brown, Q. I. Churches, C. A. Hutton, “Total Synthesis of Ustiloxin D Utilizing an Ammonia–Ugi Reaction,” J. Org. Chem., 2015, 80, 9831–9837.
J. R. Cochrane, J. M. White, U. Wille and C. A. Hutton, “Total Synthesis of Mycocyclosin,” Org. Lett. 2012, 14, 2402–2405.
Q. I. Churches, J. M. White, C. A. Hutton, “Synthesis of β,γ-Dihydroxyhomotyrosines by a Tandem Petasis–Asymmetric Dihydroxylation Approach,” Org. Lett. 2011, 13, 2900–2903.
B. T. Y. Li, J. M. White, C. A. Hutton, “Synthesis of the Leu–Trp component of the celogentin family of cyclic peptides through a C–H activation–cross-coupling strategy,” Aust. J. Chem. 2010, 63, 438–444.
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