Thiourea-Catalyzed Aminolysis of N-acyl Homoserine Lactones

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 attenua...

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Bibliographische Detailangaben
Hauptverfasser:	Bertucci, Michael A, Lee, Stephen J, Gagne, Michel r
Format:	Report
Sprache:	eng
Schlagworte:	AHL(N-ACYL HOMOSERINE LACTONES) AMINO ACIDS AMINOLYSIS BACTERIA BACTERIAL QUORUM SENSING Biochemistry CATALYSTS LACTONES LYSIS Medicine and Medical Research Organic Chemistry PE611102 Physical Chemistry POLAR PROTIC SOLVENTS RATE ENHANCEMENT SOLVENTS THIOUREA VIRULENCE
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Zusammenfassung:	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. Published in Chemical Communications, v49 n20 p2055-2057, 2013. Prepared in cooperation with the Department of Chemistry, Univ of North Carolina, Chapel Hill.