Thiourea-catalyzed aminolysis of N-acyl homoserine lactones

被引：12

作者：

Bertucci, Michael A. ^{[1
]}

Lee, Stephen J. ^{[2
]}

Gagne, Michel R. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Caudill & Kenan Labs, Chapel Hill, NC 27599 USA

[2] USA, Res Off, Res Triangle Pk, NC 27709 USA

来源：

CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 20期

关键词：

RING-OPENING AMINOLYSIS; METAL-FREE; QUORUM; ORGANOCATALYSIS; COMMUNICATION; INHIBITORS;

D O I：

10.1039/c3cc00268c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：2055 / 2057

页数：3

共 31 条

[1] Macromolecular Inhibition of Quorum Sensing: Enzymes, Antibodies, and Beyond [J].

Amara, Neri ;

Krom, Bastiaan P. ;

Kaufmann, Gunnar F. ;

Meijler, Michael M. .

CHEMICAL REVIEWS, 2011, 111 (01) :195-208

[2] Quorum sensing in bacterial virulence [J].

Antunes, L. Caetano M. ;

Ferreira, Rosana B. R. ;

Buckner, Michelle M. C. ;

Finlay, B. Brett .

MICROBIOLOGY-SGM, 2010, 156 :2271-2282

[3] A NONCATALYZED RING-OPENING AMINOLYSIS REACTION OF SESQUITERPENE LACTONES [J].

BLAY, G ;

CARDONA, L ;

GARCIA, B ;

GARCIA, CL ;

PEDRO, JR .

TETRAHEDRON LETTERS, 1994, 35 (06) :931-934

[4] Controlling infection by tuning in and turning down the volume of bacterial small-talk [J].

Cámara, M ;

Williams, P ;

Hardman, A .

LANCET INFECTIOUS DISEASES, 2002, 2 (11) :667-676

[5]

Cao Y., 2007, CHEM INFORM, V38, P15

[6] Extracellular communication in bacteria [J].

Chhabra, SR ;

Philipp, B ;

Eberl, L ;

Givskov, M ;

Williams, P ;

Cámara, M .

CHEMISTRY OF PHEROMONES AND OTHER SEMIOCHEMICALS II, 2005, 240 :279-315

[7] Synthetic analogues of the bacterial signal (quorum sensing) molecule N-(3-oxododecanoyl)-L-homoserine lactone as immune modulators [J].

Chhabra, SR ;

Harty, C ;

Hooi, DSW ;

Daykin, M ;

Williams, P ;

Telford, G ;

Pritchard, DI ;

Bycroft, BW .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (01) :97-104

[8] Structural Basis of Acyl-homoserine Lactone-Dependent Signaling [J].

Churchill, Mair E. A. ;

Chen, Lingling .

CHEMICAL REVIEWS, 2011, 111 (01) :68-85

[9] Organocatalysis mediated by (thio)urea derivatives [J].

Connon, Stephen J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (21) :5418-5427

[10] Thiourea-based bifunctional organocatalysis: Supramolecular recognition for living polymerization [J].

Dove, AP ;

Pratt, RC ;

Lohmeijer, BGG ;

Waymouth, RM ;

Hedrick, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13798-13799

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