Alcohol uncaging with fluorescence reporting:: Evaluation of o-acetoxyphenyl methyloxazolone precursors

被引:42
作者
Gagey, Nathalie [1 ]
Emond, Matthieu [1 ]
Neveu, Pierre [1 ,2 ]
Benbrahim, Chouaha [1 ]
Goetz, Bernard [1 ]
Aujard, Isabelle [1 ]
Baudin, Jean-Bernard [1 ]
Jullien, Ludovic [1 ]
机构
[1] UPMC Paris 06, ENS, CNRS, Dept Chim,UMR 8640, F-75231 Paris 05, France
[2] UPMC Paris 06 Paris 07, ENS, CNRS, Lab Phys Stat,UMR 8550, F-75231 Paris 05, France
关键词
D O I
10.1021/ol800284g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This paper evaluates a series of photolabile protecting groups with built-in fluorescence reporting. They rely on readily available o-acetoxyphenyl methyloxazolones as activated precursors. Alcohol substrates are easily caged. The resulting photoactivable esters exhibit large one- and two-photon uncaging cross sections. The alcohol substrates are quantitatively released in a 1:1 molar ratio with a strongly fluorescent coumarin coproduct that serves as a reporter to quantify substrate delivery.
引用
收藏
页码:2341 / 2344
页数:4
相关论文
共 32 条
[1]   Photo-mediated gene activation using caged RNA/DNA in zebrafish embryos [J].
Ando, H ;
Furuta, T ;
Tsien, RY ;
Okamoto, H .
NATURE GENETICS, 2001, 28 (04) :317-325
[2]   o-Nitrobenzyl photolabile protecting groups with red-shifted absorption:: Syntheses and uncaging cross-sections for one- and two-photon excitation [J].
Aujard, Isabelle ;
Benbrahim, Chouaha ;
Gouget, Marine ;
Ruel, Odile ;
Baudin, Jean-Bernard ;
Neveu, Pierre ;
Jullien, Ludovic .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (26) :6865-6879
[3]   Photolabile protecting groups and linkers [J].
Bochet, CG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (02) :125-142
[4]   Drosophila mitotic domain boundaries as cell fate boundaries [J].
Cambridge, SB ;
Davis, RL ;
Minden, JS .
SCIENCE, 1997, 277 (5327) :825-828
[5]   Microwave-mediated solventless synthesis of new derivatives of marine alkaloid Leucettamine B [J].
Chérouvrier, JR ;
Carreaux, F ;
Bazureau, JP .
TETRAHEDRON LETTERS, 2002, 43 (19) :3581-3584
[6]   4-(2'-HYDROXYPHENYLMETHYLENE)-2-PHENYLOXAZOL-5(4H)-ONE - A COMEDY OF ERRORS [J].
CORNFORTH, J ;
DU, MH .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2183-2187
[7]   SYNTHESIS, PHOTOCHEMISTRY AND ENZYMOLOGY OF 2-O-(2-NITROBENZYL)-D-GLUCOSE, A PHOTOLABILE DERIVATIVE OF D-GLUCOSE [J].
CORRIE, JET .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (18) :2161-2166
[8]  
Dakin HD, 1929, J BIOL CHEM, V82, P439
[9]  
Erlenmeyer E., 1893, Ann., V275, P1, DOI [10.1002/jlac.18932750103, DOI 10.1002/JLAC.18932750103]
[10]   Brominated 7-hydroxycoumarin-4-ylmethyls: Photolabile protecting groups with biologically useful cross-sections for two photon photolysis [J].
Furuta, T ;
Wang, SSH ;
Dantzker, JL ;
Dore, TM ;
Bybee, WJ ;
Callaway, EM ;
Denk, W ;
Tsien, RY .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (04) :1193-1200