Biocascade Synthesis of L‐Tyrosine Derivatives by Coupling a Thermophilic Tyrosine Phenol‐Lyase and L‐Lactate Oxidase. Issue 8 (18th February 2020)

• Record Type: Journal Article
• Authors: Li, Guosi; Lian, Jiazhang; Xue, Hailong; Jiang, Yiqi; Ju, Shuyun; Wu, Mianbin; Lin, Jianping; Yang, Lirong
• Is Part Of: European journal of organic chemistry. Issue 8(2020)
• Page Start: 1050
• Page End: 1054
• Publication Date: 2020-02-18
• Subjects: Biocatalysis -- Cascade reactions -- Enzyme catalysis -- Synthetic methods -- Tyrosine derivatives; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000061
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A one‐pot biocascade of two enzymatic steps catalyzed by an l ‐lactate oxidase and a tyrosine phenol‐lyase has been successfully developed in the present study. The reaction provides an efficient method for the synthesis of l ‐tyrosine derivatives, which exhibits readily available starting materials and excellent yields. In the first step, an in situ generation of pyruvate from readily available bio‐based l ‐lactate catalyzed by a highly active l ‐lactate oxidase from Aerococcus viridans (AvLOX) was developed (using oxygen as oxidant and catalase as hydrogen peroxide removing reagent). Pyruvate thus produced underwent C–C coupling with phenol derivatives as acceptor substrate using specially designed thermophilic tyrosine phenol‐lyase mutants from Symbiobacterium toebii (TTPL). Overall, this cascade avoids the high cost and easy decomposition of pyruvate and offered an efficient and environmentally friendly procedure for l ‐tyrosine derivatives synthesis. Abstract : A one‐pot biocascade of two enzymatic steps catalyzed by a l ‐lactate oxidase (AvLOX) and a designed thermophilic tyrosine‐phenol lyase (TTPL) mutant was used for the synthesis of l ‐tyrosine derivatives, in which pyruvate was in situ generated by AvLOX from readily available bio‐based l ‐lactate.