Synthesis of 2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine

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概要

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• 2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine(2), a precursor of Watasenia preluciferin(coelenterazine)(1), is widely distributed in marine bioluminescent animals. It was prepared from p-hydroxyphenylglyoxal aldoxime(5)in two steps; by condensation with α-aminophenylpropiononitrile in the presence of TiCl_4 in pyridine, followed by reduction of the resulting N-oxide(6)with Zn-AcOH in CH_2Cl_2 and produced 2, with an 89% overall yield. This procedure was linked with the facile one-step preluciferin synthesis reported in the previous paper. Thus, Watasenia preluciferin(1), frequently required for various chemiluminescent and bioluminescent studies, was coveniently synthesized in three steps from 5, with a 56% overall yield, overcoming the difficulty of obtaining in from natural sources.

• 公益社団法人日本薬学会の論文
• 2002-02-01

著者

• Kakoi Hisae

  Faculty Of Pharmacy Meijo University

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• Synthesis of 2-Amino-3-benzyl-5-(p-hydroxyphenyl)pyrazine
• Trace Characterization of the Watasenia Luciferin in Eye and Skin Photophores and in Liver of Watasenia scintillans

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