SYNTHESIS OF DEUTERATED CYCLODOPA WITH HYDROGEN/DEUTERIUM EXCHANGE

被引：3

作者：

Tachrim, Zetryana Puteri ^{[1
]}

Nakagawa, Shiori ^{[1
]}

Nakamura, Tadashi ^{[2
]}

Ohashi, Fumina ^{[1
]}

Kurokawa, Natsumi ^{[1
]}

Wakasa, Haruna ^{[1
]}

Tokoro, Yurika ^{[1
]}

Sakihama, Yasuko ^{[1
]}

Hashidoko, Yasuyuki ^{[1
]}

Suzuki, Takeyuki ^{[3
]}

Hashimoto, Makoto ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Agr, Div Appl Biosci, Kita Ku, Kita 9,Nishi 9, Sapporo, Hokkaido, Japan

[2] Obihiro Univ Agr & Vet Med, Dept Agr & Life Sci, Obihiro, Hokkaido, Japan

[3] Osaka Univ, Inst Sci & Ind Res, Div Appl Sci, Ibaraki, Osaka 5670047, Japan

来源：

HETEROCYCLES | 2019年 / 99卷 / 01期

关键词：

TRIFLUOROMETHANESULFONIC ACID;

D O I：

10.3987/COM-18-S(F)33

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：404 / 414

页数：11

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