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Biocascade Synthesis of L‐Tyrosine Derivatives by Coupling a Thermophilic Tyrosine Phenol‐Lyase and L‐Lactate Oxidase
Author(s) -
Li Guosi,
Lian Jiazhang,
Xue Hailong,
Jiang Yiqi,
Ju Shuyun,
Wu Mianbin,
Lin Jianping,
Yang Lirong
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000061
Subject(s) - chemistry , tyrosine , hydrogen peroxide , substrate (aquarium) , oxidase test , phenol , thermophile , combinatorial chemistry , catalysis , reagent , organic chemistry , biochemistry , enzyme , oceanography , geology
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.