Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 21, Issue 17, Pages 5033-5036Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2011.04.087
Keywords
Bioorthogonal chemistry; Photoclick chemistry; Dipolar cycloaddition; Tetrazoles; Fluorophores
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Funding
- National Institutes of Health [R01 GM 085092]
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We report the discovery of two long-wavelength (365 nm) photoactivatable diaryltetrazoles through screening a small library of diaryltetrazoles that were designed using a 'scaffold hopping' strategy. A naphthalene-derived tetrazole showed excellent reactivity in the photoinduced cycloaddition reaction with methyl methacrylate under 365 nm photoirradiation in acetonitrile PBS buffer mixture. Besides, the brightly fluorescent pyrazoline cycloadducts that were formed further increase the potential utility of these new diaryltetrazoles as 'photoclick' reagents and as reporters in biological studies. (C) 2011 Elsevier Ltd. All rights reserved.
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