Issue 20, 2013
From the journal:

Chemical Communications

Thiourea-catalyzed aminolysis of N-acyl homoserine lactones†

Michael A. Bertucci,a   Stephen J. Leeb  and  Michel R. Gagné*a  

* Corresponding authors

a Department of Chemistry, University of North Carolina at Chapel Hill, Campus Box 3290, Caudill and Kenan Laboratories, Chapel Hill, NC, USA
E-mail: mgagne@unc.edu
Fax: +1 919-962-2388
Tel: +1 919-962-0278

b US Army Research Office, P.O. Box 12211, Research Triangle Park, NC, USA

Abstract

Thiourea catalysts accelerate aminolysis of N-acyl homoserine lactones (AHLs), molecules integral to bacterial quorum sensing. The catalysts afford rate enhancement of up to 10 times the control in CD3CN. Mild catalysis in other polar aprotic solvents is still observed, while the activity is attenuated in polar protic solvents.

Graphical abstract: Thiourea-catalyzed aminolysis of N-acyl homoserine lactones

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Article information

DOI
https://doi.org/10.1039/C3CC00268C
Article type
Communication
Submitted
30 Nov 2012
Accepted
22 Jan 2013
First published
23 Jan 2013

Chem. Commun., 2013,49, 2055-2057

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Thiourea-catalyzed aminolysis of N-acyl homoserine lactones

M. A. Bertucci, S. J. Lee and M. R. Gagné, Chem. Commun., 2013, 49, 2055 DOI: 10.1039/C3CC00268C

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