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Paper | Special issue | Vol 99, No. 1, 2019, pp.404-414
Published online, 24th October, 2018
DOI: 10.3987/COM-18-S(F)33
Synthesis of Deuterated CycloDOPA with Hydrogen/Deuterium Exchange

Zetryana Puteri Tachrim, Shiori Nakagawa, Tadashi Nakamura, Fumina Ohashi, Natsumi Kurokawa, Haruna Wakasa, Yurika Tokoro, Yasuko Sakihama, Yasuyuki Hashidoko, Takeyuki Suzuki, and Makoto Hashimoto*

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


CycloDOPA (5,6-dihydroxy-indoline-2-carboxylic acid, leukodopachrome) is one of metabolites derived from tyrosine, one of intermediate in melanin formation (mammalian) and betanidin main skeleton (betalain pigment in plant). Synthesis of deuterated cyclodopa via hydrogen/deuterium exchange by utilization of deuterium chloride (DCl) and deuterated triflic acid (TfOD) are reported. The novel fully deuterated aromatic cycloDOPA derivative can be formed depending on temperature and time of H/D exchange condition. The complete study of H/D exchange resulted in the selective deuterium between 4- and/or 7-position of aromatic hydrogen of cycloDOPA.