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Ene Reductase Enzymes for the Aromatisation of Tetralones and Cyclohexenones to Naphthols and Phenols
Author(s) -
Kelly Paul P.,
Lipscomb David,
Quinn Derek J.,
Lemon Ken,
Caswell Jill,
Spratt Jenny,
Kosjek Birgit,
Truppo Matthew,
Moody Thomas S.
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500818
Subject(s) - chemistry , tetralones , phenols , yield (engineering) , biocatalysis , ionone , organic chemistry , substrate (aquarium) , enzyme , aqueous solution , organic solvent , catalysis , reaction mechanism , materials science , oceanography , metallurgy , geology , chemical engineering , engineering
Ene reductases (EREDs) have great potential as oxidation biocatalysts, as demonstrated by their efficient conversion of a number of tetralones to the corresponding naphthols. Of 96 enzymes tested, 57 were able to produce 2‐naphthol in this way. Further tests with substituted tetralones revealed typically high conversions up to >99%. The reactions were performed under mild conditions in aqueous buffer with only co‐solvent, biocatalyst and oxidation substrate required for conversion. Production of a methoxy‐substituted naphthol was also successfully performed on a gram scale, with 91% yield. This methodology provides a new avenue to produce substituted naphthols as valuable building blocks, with the possibility to extend the approach to the production of phenols also being demonstrated.