Synthesis of azide-fluoro-dehydrocoelenterazine analog as a photoaffinity-labeling probe and photolysis of azide-fluoro-coelenterazine |
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| Authors: | Masaki Kuse Nobuhiro Kondo Minoru Isobe |
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| Affiliation: | a Chemical Instrument Division, RCMS, Nagoya University, Chikusa-ku, Furo-cho, 4648602 Nagoya, Japan
b Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, 464-8601 Nagoya, Japan |
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| Abstract: | A photosensitive azide-fluoro-dehydrocoelenterazine analog (Az-F-DCT) was synthesized, starting from 4-fluorophenylacetic acid, as a photoaffinity-labeling probe in order to analyze symplectin active site. To examine the photo-reactivity of Az-F-DCT, azide-fluoro-coelenterazine analog (Az-F-CT) was used as a potent symplectin chromophore model. Photolysis of Az-F-CT in 2,2,2-trifluoroethanol afforded nitrene intermediate to give an insertion product. The structure of this product was confirmed through spectroscopic analyses particularly by using a proton/deuterium (H/D) exchange experiments with ESI-Q-TOF-MS and -MS/MS measurement. |
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| Keywords: | Coelenterazine Deuteriation MS Exchangeable protons Azide-fluoro-phenyl Photoaffinity probe |
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