棉酚
化学
对映体
阿托品
立体化学
生物合成
生物化学
酶
作者
Isabelle Effenberger,Zhang Bin,Ling Li,Qiang Wang,Yuxiu Liu,Iris Klaiber,Jens Pfannstiel,Qingmin Wang,Andreas Schaller
标识
DOI:10.1002/anie.201507543
摘要
Gossypol is a defense compound in cotton plants for protection against pests and pathogens. Gossypol biosynthesis involves the oxidative coupling of hemigossypol and results in two atropisomers owing to hindered rotation around the central binaphthyl bond. (+)-Gossypol predominates in vivo, thus suggesting stereochemically controlled biosynthesis. The aim was to identify the factors mediating (+)-gossypol formation in cotton and to investigate their potential for asymmetric biaryl synthesis. A dirigent protein from Gossypium hirsutum (GhDIR4) was found to confer atropselectivity to the coupling of hemigossypol in presence of laccase and O2 as an oxidizing agent. (+)-Gossypol was obtained in greater than 80% enantiomeric excess compared to racemic gossypol in the absence of GhDIR4. The identification of GhDIR4 highlights a broader role for DIRs in plant secondary metabolism and may eventually lead to the development of DIRs as tools for the synthesis of axially chiral binaphthyls.
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