The donor-acceptor biphenyl platform: a versatile chromophore for the engineering of highly efficient two-photon sensitive photoremovable protecting groups.
Different photoremovable protecting groups in the o-nitrobenzyl, phenacyl, and 2-(o-nitrophenyl)propyl series with a donor-acceptor biphenyl backbone, known to display excellent two-photon absorption cross-sections, were investigated in order to develop efficient two-photon sensitive photoremovable protecting groups. The 2-(o-nitrophenyl)propyl series was a more versatile platform to increase the two-photon sensitivity of photoremovable protecting groups, leading to the p-alkoxy and p-bisalkylamino-4-nitro-[1,1'-biphenyl]-3-yl)propyl derivatives: PENB and EANBP respectively. Those two photoremovable protecting groups are to date the best caging groups for two-photon excitation at 800 and 740 nm respectively, offering attracting perspectives in chemical biology.
Laboratoire de Conception et Application de Molécules Bioactives, UMR 7199, CNRS/UDS, Faculté de Pharmacie, Illkirch, France. specht@bioorga.u-strasbg.fr
Alexandre
A
Specht
Frédéric
F
Bolze
Loïc
L
Donato
Cyril
C
Herbivo
Sébastien
S
Charon
David
D
Warther
Sylvestre
S
Gug
Jean-François
JF
Nicoud
Maurice
M
Goeldner
D001713:Biphenyl Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000737:chemistry*; D010782:Photolysis; D017785:Photons
D001713:Biphenyl Compounds; D009578:Nitrobenzenes