Development of a new nonpeptidic self-immolative spacer. Application to the design of protease sensing fluorogenic probes.
The design and synthesis of novel self-immolative spacer systems aiming at the release of phenol-containing compounds are described. The newly designed traceless linkers proved to be conveniently stable under physiological conditions and operate through spontaneous decomposition of an hemithioaminal intermediate under neutral aqueous conditions. Their utility was then illustrated by the preparation of original fluorogenic substrates of penicillin amidase whose strong fluorescence is unveiled through enzyme-initiated domino reactions.
Meyer
Yves
Y
Equipe de Chimie Bio-Organique, Université de Rouen, Place Emile Blondel, 76821 Mont-Saint-Aignan, France.
Richard
Jean-Alexandre
JA
Massonneau
Marc
M
Renard
Pierre-Yves
PY
Romieu
Anthony
A
D002851:Chromatography, High Pressure Liquid; D005456:Fluorescent Dyes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010447:Peptide Hydrolases / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D005456:Fluorescent Dyes; D010455:Peptides; D010447:Peptide Hydrolases