Biosynthesis of violacein: a genuine intermediate, protoviolaceinic acid, produced by VioABDE, and insight into VioC function

Kouhei Shinoda; Takuji Hasegawa; Hiroaki Sato; Masaaki Shinozaki; Hirotomo Kuramoto; Yosuke Takamiya; Tsutomu Sato; Naoki Nikaidou; Takeshi Watanabe; Tsutomu Hoshino

doi:10.1039/B705358D

Biosynthesis of violacein: a genuine intermediate, protoviolaceinic acid, produced by VioABDE, and insight into VioC function†

Kouhei Shinoda,^a Takuji Hasegawa,^a Hiroaki Sato,^a Masaaki Shinozaki,^a Hirotomo Kuramoto,^a Yosuke Takamiya,^a Tsutomu Sato,^a Naoki Nikaidou,^a Takeshi Watanabe^a and Tsutomu Hoshino*^a

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^a Department of Applied Biological Chemistry, Faculty of Agriculture, and Graduate School of Science and Technology, Niigata University, Ikarashi, Niigata, Japan
E-mail: hoshitsu@agr.niigata-u.ac.jp
Fax: +81-25-262-6854

Abstract

A biosynthetic intermediate of violacein produced by the mixed enzymes of VioABDE was elucidated to be 5-(5-hydroxy-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2-carboxylic acid, named protoviolaceinic acid, indicating that VioC, responsible for the final biosynthetic step, works to oxygenate at the 2-position of the right side indole ring, and that the oxygenation reaction to form the central pyrrolidone core proceeds in a non-enzymatic fashion.

Chemical Communications

Biosynthesis of violacein: a genuine intermediate, protoviolaceinic acid, produced by VioABDE, and insight into VioC function†

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Biosynthesis of violacein: a genuine intermediate, protoviolaceinic acid, produced by VioABDE, and insight into VioC function

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