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Selective Pathways for Carbon-Nitrogen Bond Cleavage

Project description

New ways to break down molecules opens the door to new ways to make them too

Carbon chemistry is invaluable to fields from pharmaceutical development to plastics and polymer manufacturing. Developing novel carbon-based compounds or compounds that mimic important natural ones can be simplified by using carbon-containing feedstocks from which atoms are removed and functional groups added in their places. Amines, molecules containing carbon bound to nitrogen, are widely available and highly diverse, and therefore among the most important building blocks in organic chemistry. The EU-funded SCAN project is developing new ways to cleave carbon–nitrogen bonds, paving the way for novel catalytic transformations and products.

Objective

Amines are ubiquitous across natural products, pharmaceuticals, polymers and biomolecules. The number of commercially available amines, from simple to complex, makes them one of the most accessible native functional groups. Therefore, they represent an attractive feedstock for the preparation of functionalized molecules through C-N bond activation.
Nature long ago developed protocols to promote oxidative deamination reactions. Inspired by this approach, SCAN (Selective Pathways for CArbon-Nitrogen Bond Cleavage) is designed to open new directions in the field of C-N bond cleavage by unlocking the oxidative deamination pathway. To achieve this goal, the following specific objectives are proposed:
1) Design of redox-active amines capable of undergoing oxidative C-N cleavage.
2) Development of novel oxidative deaminations using photoredox and metallaphotoredox catalysis.
3) Site-selective modifications of peptides through photocatalyzed oxidative deaminations.

The successful implementation will allow the use of one of the most readily available functional groups in a myriad of novel catalytic transformations, including for the first time asymmetric catalysis. The prevalence of alkyl amines in pharmaceuticals makes SCAN an ideal tool for late stage functionalization and molecular editing of complex molecules. Moreover, this reactivity could be used to achieve site-selective modifications of NH2 groups in peptides via C-N bond cleavage, which would have a profound impact in the fields of chemistry and chemical biology. Together, the conceptual novelty, the ability to pursue multiple complementary approaches at once, and the various potential applications will ensure high impact of this project in both the academic and industrial communities.

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Keywords

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Programme(s)

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Topic(s)

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Funding Scheme

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ERC-COG - Consolidator Grant

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Call for proposal

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(opens in new window) ERC-2020-COG

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Host institution

UNIVERSIDAD AUTONOMA DE MADRID
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.

€ 2 000 000,00
Address
CALLE EINSTEIN 3 CIUDAD UNIV CANTOBLANCO RECTORADO
28049 MADRID
Spain

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Region
Comunidad de Madrid Comunidad de Madrid Madrid
Activity type
Higher or Secondary Education Establishments
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Total cost

The total costs incurred by this organisation to participate in the project, including direct and indirect costs. This amount is a subset of the overall project budget.

€ 2 000 000,00

Beneficiaries (1)

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