Alcohol uncaging with fluorescence reporting: evaluation of o-acetoxyphenyl methyloxazolone precursors.
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.
Gagey
Nathalie
N
Département de Chimie and Laboratoire de Physique Statistique, Ecole Normale Supérieure, Paris Cedex 05, France.
Emond
Matthieu
M
Neveu
Pierre
P
Benbrahim
Chouaha
C
Goetz
Bernard
B
Aujard
Isabelle
I
Baudin
Jean-Bernard
JB
Jullien
Ludovic
L
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry; D005453:Fluorescence; D008958:Models, Molecular; D015394:Molecular Structure; D010081:Oxazolone / Q000031:analogs & derivatives* / Q000737:chemistry*; D010777:Photochemistry; D013237:Stereoisomerism
D000438:Alcohols; D003374:Coumarins; D010081:Oxazolone