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Kaoru Fuji's Special Issues, Vol. 101, No. 1, 2020

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Short Paper | Special issue | Vol 101, No. 1, 2020, pp. 357 - 362
Published online: 28th August, 2019
DOI: 10.3987/COM-19-S(F)28
Hydrogen-Deuterium Exchange of Histidine and Histamine with Deuterated Trifluoromethanesulfonic Acid

Zetryana Puteri Tachrim, Natsumi Kurokawa, Yurika Tokoro, and Makoto Hashimoto*

*Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-9, Nishi-9, Kita-ku, Sapporo, Hokkaido 060-8589, Japan

Abstract

Histidine and its decarboxylated metabolite, histamine, containing imidazole ring, play an important role for biological activity. Deuterated trifluoromethanesulfonic acid (TfOD) is one of the acid hydrogen-deuterium exchange reagents for aromatic compounds. Hydrogen-deuterium exchange of histidine and histamine with TfOD were examined in this report.

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Short Paper | Special issue | Vol 101, No. 1, 2020, pp. 363 - 372
Published online: 11th September, 2019
DOI: 10.3987/COM-19-S(F)33
Construction of Quaternary Carbon Center by the Reaction of Aza-o-Quinone Methide Mediated Carbocation Intermediate

Yukiko Karuo, Shintaro Dousei, Minori Sakamoto, Atsushi Tarui, Kazuyuki Sato, Kentaro Kawai, and Masaaki Omote*

*Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101 , Japan

Abstract

Reactions of carbocationic intermediate corresponding to aza-o-quinone methide with indoles to construct quaternary carbon center were described. Treatment of N-tosylated 2-(2-aminophenyl)propan-2-ol with iron(III) chloride provided tertiary benzylic carbocation intermediate possible to isomerize to the corresponding aza-o-quinone methide. The electron-deficient intermediate enabled to undergo nucleophilic attack by indoles, representing the first example of intermolecular formation of quaternary carbon center using aza-o-quinone methide mediated carbocation intermediate.

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32 data found. 31 - 32 listedFirst Previous