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Unlocking the Antitubercular Mode of Action of Asperterpenoid through Total Synthesis

Project description

Total synthesis of asperterpenoid could point to novel treatments for tuberculosis

According to the World Health Organization, 1.5 million people die every year from tuberculosis, a preventable and curable disease. Multi-drug resistant strains of Mycobacterium tuberculosis, the pathogen causing tuberculosis, are on the rise. Asperterpenoid has a unique and highly carbon skeleton that strongly inhibits a protein secreted by M. tuberculosis that aids human host infection. Its total synthesis has been elusive but knowing more about it is necessary to better understand asperterpenoid’s properties and synthesise natural products with similar antitubercular properties. With the support of the Marie Skłodowska-Curie Actions programme, the Asperterpenoid project aims to accomplish all these goals, synthesising asperterpenoid from bio-renewable sitolactone using a key intermolecular reductive titanium-mediated Giese addition reaction.

Objective

The rise of multi-drug resistant strains of Mycobacterium tuberculosis, the pathogen responsible for the infectious disease tuberculosis, calls for research into novel antitubercular scaffolds and targets. Asperterpenoid is a rare sesterterpenoid with a unique and highly complex 5/7(3)/6/5 ring-fused carbon skeleton that strongly inhibits tyrosine phosphatase B, a virulence factor protein secreted by M. tuberculosis that aids human host infection. To date, total synthesis of asperterpenoid has not been accomplished. We propose a modular synthesis of asperterpenoid from biorenewable sitolactone using a key intermolecular reductive titanium mediated Giese addition reaction. The scope of this privileged reaction will be expanded by investigating selected epoxide substrates and Michael acceptors. We anticipate that the synthetic strategy to asperterpenoid can be extrapolated to prepare variecolin, a structurally related sesterterpenoid that has been subject of several studies but never reached by chemical synthesis. Based on its structural similarity to asperterpenoid, we expect that variecolin will also exhibit antitubercular activity. We plan to study the known antitubercular activity of asperterpenoid by structural diversification and its mechanism of action by a chemical biology tools such as molecular imaging. We also plan to test variecolin for antitubercular activity. The action is expected to contribute to new synthetic tools and strategies to prepare rare sesterterpenoid natural products, a better understanding of the promising antitubercular properties of asperterpenoid, and to demonstrate that variecolin exhibits similar bioactive behaviour.

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Topic(s)

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HORIZON-TMA-MSCA-PF-GF - HORIZON TMA MSCA Postdoctoral Fellowships - Global Fellowships

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Call for proposal

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(opens in new window) HORIZON-MSCA-2023-PF-01

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Coordinator

AARHUS UNIVERSITET
Net EU contribution

Net EU financial contribution. The sum of money that the participant receives, deducted by the EU contribution to its linked third party. It considers the distribution of the EU financial contribution between direct beneficiaries of the project and other types of participants, like third-party participants.

€ 286 191,36
Address
NORDRE RINGGADE 1
8000 Aarhus C
Denmark

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Region
Danmark Midtjylland Østjylland
Activity type
Higher or Secondary Education Establishments
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Total cost

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