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...

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Bibliographic Details
Published inOrganic letters Vol. 10; no. 8; pp. 1517 - 1520
Main Authors Meyer, Yves, Richard, Jean-Alexandre, Massonneau, Marc, Renard, Pierre-Yves, Romieu, Anthony
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.04.2008
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Chromatography, High Pressure Liquid
Fluorescent Dyes - chemistry
Magnetic Resonance Spectroscopy
Peptide Hydrolases - chemistry
Peptides - chemistry
Physical Sciences
Science & Technology
Spectrometry, Fluorescence
TRACELESS
PRODRUG
TRIMETHYL LOCK
SOLID SUPPORTS
CHEMISTRY
GENERATION
LINKER
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol800198f