Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor,Green Chemistry

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Environment-friendly and efficient synthesis of 2-aminobenzo-xazoles and 2-aminobenzothiazoles catalyzed by Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor
Green Chemistry ( IF 9.3 ) Pub Date : 2021-09-06 , DOI: 10.1039/d1gc02533c
Yaning Xu ₁ , Fengxi Li ₁ , Nan Zhao ₁ , Jiali Su ₁ , Chunyu Wang ₂ , Ciduo Wang ₁ , Zhengqiang Li ₁ , Lei Wang ₁

Affiliation

In this study, an environment-friendly and efficient artificial Vitreoscilla hemoglobin (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. We demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, we provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, we indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions.

中文翻译：

玻璃体血红蛋白结合钴卟啉辅因子催化环保高效合成2-氨基苯并恶唑和2-氨基苯并噻唑

在这项研究中，报道了一种用于合成 2-氨基苯并恶唑和 2-氨基苯并噻唑的环境友好且高效的人工玻璃体血红蛋白 (VHb)。我们展示了一种基于表达的卟啉替代策略来生产含有钴卟啉而不是天然氯化血红素的 VHb，它可以催化相应的 2-氨基苯并恶唑和 2-氨基苯噻唑的氧化环化，在有氧条件下在水中的产率高达 97% 和 4850 次催化转化. 因此，我们提供了一种绿色温和的合成 2-氨基苯并恶唑和 2-氨基苯并噻唑的方法。此外，我们指出了卟啉配体取代作为一种策略来调整和增强血红素蛋白在非自然反应中的催化特性的价值。

更新日期：2021-09-24

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