New synthetic strategies to small cyclic peptides

Grant number: DP180101804 | Funding period: 2018 - 2020

Completed

Abstract

This project aims to invent new synthetic strategies that enable chemical manipulation of small cyclic peptides, a promising class of biologically active molecules with high metabolic stability. Combining theory and practice, this project will develop novel acyl transfer reactions that will allow traceless, site-selective, ring expansion and contraction of small cyclic peptides. This project will result in new synthetic methodology that will simplify the synthesis of an important class of small drug-like molecules. This will provide significant benefits, such as a breakthrough in the synthetic approach to small cyclic peptides, which will strengthen Australia’s international standing in pept..

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Related publications (9)

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Depsipeptide synthesis using a late-stage Ag(i)-promoted macrolactonisation of peptide thioamides

Sadegh Shabani, Craig A Hutton

2021-02-25

Macrolactonisation of peptides to generate cyclic depsipeptides is often challenging due to the low nucleophilicity of hydroxyl gr..

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Ring Expansion of Thiolactams via Imide Intermediates: An Amino Acid Insertion Strategy

Jing Shang, Varsha J Thombare, Carlie L Charron, Uta Wille, Craig A Hutton

2020-12-22

The Ag(I)-promoted reaction of thiolactams with N-Boc amino acids yields an N-(α-aminoacyl) lactam that can rearrange through an a..

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Total Synthesis of the Putative Structure of Asperipin-2a and Stereochemical Reassignment

Sadegh Shabani, Jonathan M White, Craig A Hutton

2020-10-02

The total synthesis of the putative structure of asperipin-2a is described. The synthesis features ether cross-links between the p..

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Total Synthesis of Seongsanamide B

Sadegh Shabani, Craig A Hutton

2020-06-05

The first total synthesis of the bicyclic depsipeptide natural product seongsanamide B is described. The successful approach emplo..

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Celogentin mimetics as inhibitors of tubulin polymerization

Varsha J Thombare, James A Holden, Eric C Reynolds, Neil M O'Brien-Simpson, Craig A Hutton

2020-03-01

Bicyclic analogues of celogentin C have been synthesized in which the side chain-side chain cross-links are replaced by thioether ..

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Structure-Activity Relationships of cyclo(L-Tyrosyl-L-tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct

Sunnia Rajput, Kirsty J McLean, Harshwardhan Poddar, Irwin R Selvam, Gayathri Nagalingam, James A Triccas, Colin W Levy, Andrew W Munro, Craig A Hutton

2019-11-14

A series of analogues of cyclo(l-tyrosyl-l-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been syn..

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Rapid, Traceless, Ag I ‐Promoted Macrocyclization of Peptides Possessing an N‐Terminal Thioamide

Varsha J Thombare, Craig A Hutton

2019-04-01

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Rapid, Traceless, Ag-I-Promoted Macrocyclization of Peptides Possessing an N-Terminal Thioamide

Varsha J Thombare, Craig A Hutton

2019-04-01

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Synthesis of the C-Terminal Macrocycle of Asperipin-2a

Sadegh Shabani, Jonathan M White, Craig A Hutton

2019-03-15