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Simple and Stereocontrolled Preparation of Benzoylated Phenylalanine Using Friedel–Crafts Reaction in Trifluoromethanesulfonic Acid for Photoaffinity Labeling

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/53249

Title: Simple and Stereocontrolled Preparation of Benzoylated Phenylalanine Using Friedel–Crafts Reaction in Trifluoromethanesulfonic Acid for Photoaffinity Labeling
Authors: Hashimoto, Makoto Browse this author →KAKEN DB
Murai, Yuta Browse this author
Wang, Lei Browse this author
Muto, Yasuyuki Browse this author
Sakihama, Yasuko Browse this author →KAKEN DB
Hashidoko, Yasuyuki Browse this author →KAKEN DB
Hatanaka, Yasumaru Browse this author →KAKEN DB
Keywords: Photoaffinity label
Benzophenone
Diazirine
Phenylalanine
Friedel-Crafts reaction
Issue Date: Sep-2013
Publisher: Japan Institute of Heterocyclic Chemistry
Journal Title: HETEROCYCLES
Volume: 87
Issue: 10
Start Page: 2119
End Page: 2126
Publisher DOI: 10.3987/COM-13-12815
Abstract: Simple and stereocontrolled preparation of benzoylated phenylalanine derivatives from optically pure phenylalanine using Friedel-Crafts reaction in trifluoromethanesulfonic acid (TfOH) is reported; these derivatives are useful for photoaffinity labeling. Protected or unprotected phenylalanine derivatives were converted to benzoyl derivatives in TfOH at room temperature in a short time without loss of optical purity. The reaction condition was applied to synthesize novel photoreactive phenylalanine derivative, which has two photophores (benzophenone and diazirine). The detail analysis of photo-irradiation for two different photophores contained phenylalanine derivative was also investigated.
Type: article (author version)
URI: http://hdl.handle.net/2115/53249
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 橋本 誠

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