Biocatalytic One-Pot Synthesis of l-Tyrosine Derivatives from Monosubstituted Benzenes, Pyruvate, and Ammonia

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• 作者：Alexander Dennig ; Eduardo Busto ; Wolfgang Kroutil ; Kurt Faber
• 刊名：ACS Catalysis
• 出版年：2015
• 出版时间：December 4, 2015
• 年：2015
• 卷：5
• 期：12
• 页码：7503-7506
• 全文大小：278K
• ISSN：2155-5435

文摘

l-Tyrosine derivatives were obtained in >97% ee via a biocatalytic one-pot two-step cascade using substituted benzenes, pyruvate, and NH₃ as starting materials. In the first step, monosubstituted arenes were regioselectively hydroxylated in the o-position by monooxygenase P450 BM3 (using O₂ as oxidant with NADPH-recycling) to yield the corresponding phenols, which subsequently underwent C鈥揅 coupling and simultaneous asymmetric amination with pyruvate and NH₃ using tyrosine phenol lyase to furnish l-DOPA surrogates in up to 5.2 g L^鈥?. Instead of analytically pure arenes, crude aromatic gasoline blends containing toluene were used to yield 3-methyl-l-tyrosine in excellent yield (2 g L^鈥?) and >97% ee.