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b-lactams C-H activation

Discovery of novel β-lactam analogs oriented to control multidrug-resistant bacteria enabled by Pd-catalyzed C–H activation of aliphatic amines

Total Cost €

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EC-Contrib. €

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Partnership

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 Outcomes and results

 b-lactams C-H activation project word cloud

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Project "b-lactams C-H activation" data sheet

The following table provides information about the project.

Coordinator		 THE CHANCELLOR MASTERS AND SCHOLARSOF THE UNIVERSITY OF CAMBRIDGE 

Organization address
address: TRINITY LANE THE OLD SCHOOLS
city: CAMBRIDGE
postcode: CB2 1TN
website: www.cam.ac.uk

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.
 Coordinator Country United Kingdom [UK]
 Project website http://www-gaunt.ch.cam.ac.uk/
 Total cost 183˙454 €
 EC max contribution 183˙454 € (100%)
 Programme 1. H2020-EU.1.3.2. (Nurturing excellence by means of cross-border and cross-sector mobility)
 Code Call H2020-MSCA-IF-2014
 Funding Scheme MSCA-IF-EF-ST
 Starting year 2015
 Duration (year-month-day) from 2015-05-01   to  2017-04-30

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    THE CHANCELLOR MASTERS AND SCHOLARSOF THE UNIVERSITY OF CAMBRIDGE UK (CAMBRIDGE) coordinator 183˙454.00

Map

 Project objective

In Europe, infections caused by multidrug-resistant bacteria lead to more than 25,000 deaths and expenses of billions of euros per year. These numbers dramatically increase when the rest of the world is taken into consideration. Shockingly, the pace of production of new antibiotics to control such microorganisms is stagnating. Therefore, developing new synthetic tools that enable the synthesis of scaffolds with potential antibiotic properties is crucial. Metal catalysed C–H activation represents a versatile tool for building chemical complexity. It mostly relies on directing functional groups to functionalize C–H bonds. Recently, Professor Gaunt at the University of Cambridge has uncovered a new C–H activation mode that enables the conversion of hindered amines into β-lactams. The first aim of this project is to develop this new reactivity mode into a versatile transformation that is able to convert a variety of cyclic and acyclic amines into substituted β-lactam scaffolds. To accomplish this goal, a multi parallel platform based on mass spectrometry, relying either on standard high-throughput procedures or flow chemistry, will be implemented and used to screen a large number of conditions to expand the scope of this new pathway for β-lactams. The flow chemistry system for reaction evaluation will be design in collaboration with Professors Alexei Lapkin (Dept. Chemical Engineering and Biotechnology) and Steve Ley (Chemistry Dept.) from the University of Cambridge. The readily discovered new conditions for C–H activation will then be employed to synthesize a plethora of β-lactams and β-sultam analogs starting from simple secondary amines. Finally, in collaboration with Professor David Spring (Chemistry Dept. University of Cambridge), the bioactivity of the resulting scaffolds will be evaluated against multidrug-resistant bacteria.

 Publications

year authors and title journal last update
List of publications.
2017 Matthew James Gaunt, Jaime Cabrera-Pardo, Aaron Trowbridge, Manuel Nappi, Kyohei Ozaki
Selective Pd(II)-Catalyzed Carbonylation of Methylene beta-C-H Bonds in Aliphatic Amines
published pages: , ISSN: 1433-7851, DOI: 10.1002/anie.201706303 		Angewandte Chemie International Edition 2019-07-23

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