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Kinetic Resolution of sec-Thiols by Enantioselective Oxidation with Rationally Engineered 5-(Hydroxymethyl) furfural Oxidase
- Source :
- Angewandte Chemie-International Edition, 57(11):anie.201713189, 2864-2868. WILEY-V C H VERLAG GMBH
- Publication Year :
- 2018
- Publisher :
- WILEY-V C H VERLAG GMBH, 2018.
-
Abstract
- Various flavoprotein oxidases were recently shown to oxidize primary thiols. Herein, this reactivity is extended to sec-thiols by using structure-guided engineering of 5-(hydroxymethyl) furfural oxidase (HMFO). The variants obtained were employed for the oxidative kinetic resolution of racemic sec-thiols, thus yielding the corresponding thioketones and nonreacted R-configured thiols with excellent enantioselectivities (E >= 200). The engineering strategy applied went beyond the classic approach of replacing bulky amino acid residues with smaller ones, as the active site was additionally enlarged by a newly introduced Thr residue. This residue established a hydrogen-bonding interaction with the substrates, as verified in the crystal structure of the variant. These strategies unlocked HMFO variants for the enantioselective oxidation of a range of sec-thiols.
- Subjects :
- Models, Molecular
oxidation
THIOETHERS
enzymes
010402 general chemistry
Furfural
01 natural sciences
Catalysis
Kinetic resolution
chemistry.chemical_compound
Residue (chemistry)
FLAVOPROTEIN OXIDASES
Escherichia coli
Point Mutation
Hydroxymethyl
Furaldehyde
Sulfhydryl Compounds
kinetic resolution
AMINO-ACID OXIDASE
ASYMMETRIC-SYNTHESIS
thiols
Oxidase test
BIOCATALYSIS
biology
010405 organic chemistry
Enantioselective synthesis
Active site
Hydrogen Bonding
Stereoisomerism
General Chemistry
Combinatorial chemistry
STEREOINVERSION
REAGENT
0104 chemical sciences
Kinetics
chemistry
Biocatalysis
biology.protein
Mutagenesis, Site-Directed
Oxidoreductases
Oxidation-Reduction
Subjects
Details
- Language :
- English
- ISSN :
- 15213773 and 14337851
- Volume :
- 57
- Issue :
- 11
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie - International Edition
- Accession number :
- edsair.doi.dedup.....4ca1bcdc9902b8d4587d756cfb219ed8