β-lactones as privileged structures for the active-site labeling of versatile bacterial

被引:139
作者
Boettcher, Thomas [1 ]
Sieber, Stephan A. [1 ]
机构
[1] Univ Munich, CIPSM, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
biomimetic synthesis; enzymes; lactones; medicinal chemistry; proteomics;
D O I
10.1002/anie.200705768
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A chemical proteomic strategy has been applied directly to bacterial proteomes, and b-lactones have been identified as important natural product derivatives with a high affinity to various enzyme classes (see picture). This approach may serve as a potent tool for the identification of novel antibacterial targets, the study of their function, and the definition of novel lead structures for the design of enzyme inhibitors. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4600 / 4603
页数:4
相关论文
共 22 条
[1]   Proteomic profiling of mechanistically distinct enzyme classes using a common chemotype [J].
Adam, GC ;
Sorensen, EJ ;
Cravatt, BF .
NATURE BIOTECHNOLOGY, 2002, 20 (08) :805-809
[2]   ANTIBIOTIC 1233A - FUNGAL BETA LACTONE [J].
ALDRIDGE, DC ;
GILES, D ;
TURNER, WB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (23) :3888-&
[3]   Bacterial proteomics and its role in antibacterial drug discovery [J].
Brötz-Oesterhelt, H ;
Bandow, JE ;
Labischinski, H .
MASS SPECTROMETRY REVIEWS, 2005, 24 (04) :549-565
[4]   Targeting virulence: a new paradigm for antimicrobial therapy [J].
Clatworthy, Anne E. ;
Pierson, Emily ;
Hung, Deborah T. .
NATURE CHEMICAL BIOLOGY, 2007, 3 (09) :541-548
[5]   A PRACTICAL AND EFFICIENT METHOD FOR THE SYNTHESIS OF BETA-LACTONES [J].
DANHEISER, RL ;
NOWICK, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) :1176-1185
[6]   Mechanism-based profiling of enzyme families [J].
Evans, Michael J. ;
Cravatt, Benjamin F. .
CHEMICAL REVIEWS, 2006, 106 (08) :3279-3301
[7]   The ClpP serine protease is essential for the intracellular parasitism and virulence of Listeria monocytogenes [J].
Gaillot, O ;
Pellegrini, E ;
Bregenholt, S ;
Nair, S ;
Berche, P .
MOLECULAR MICROBIOLOGY, 2000, 35 (06) :1286-1294
[8]   Epoxide electrophiles as activity-dependent cysteine protease profiling and discovery tools [J].
Greenbaum, D ;
Medzihradszky, KF ;
Burlingame, A ;
Bogyo, M .
CHEMISTRY & BIOLOGY, 2000, 7 (08) :569-581
[9]   Contribution of the ATP-dependent protease ClpCP to the autolysis and virulence of Streptococcus pneumoniae [J].
Ibrahim, YM ;
Kerr, AR ;
Silva, NA ;
Mitchell, TJ .
INFECTION AND IMMUNITY, 2005, 73 (02) :730-740
[10]   Cleavage of β-lactone ring by serine protease.: Mechanistic implications [J].
Kim, DH ;
Park, JI ;
Chung, SJ ;
Park, JD ;
Park, NK ;
Han, JH .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2553-2560