Journal
CHEMCATCHEM
Volume 7, Issue 15, Pages 2313-2317Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201500218
Keywords
aldehyde oxidase; amino alcohols; cascade reactions; enzyme catalysis; lactams
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Funding
- Innovative Medicines Initiative Joint Undertaking [115360]
- European Union
- EFPIA
- Science and Industry Endowment (SIEF)
- Engineering and Physical Sciences Research Council (EPSRC)
- Royal Society Wolfson Merit Award
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The use of selected engineered galactose oxidase (GOase) variants for the oxidation of amino alcohols to aldehydes under mild conditions in aqueous systems is reported. GOase variant F-2 catalyses the regioselective oxidation of N-carbobenzyloxy (Cbz)-protected 3-amino-1,2-propanediol to the corresponding -hydroxyaldehyde which was then used in an aldolase reaction. Another variant, M3-5, was found to exhibit activity towards free and N-Cbz-protected aliphatic and aromatic amino alcohols allowing the synthesis of lactams such as 3,4-dihydronaphthalen-1(2H)-one, 2-pyrrolidone and valerolactam in one-pot tandem reactions with xanthine dehydrogenase (XDH) or aldehyde oxidase (PaoABC).
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