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Literature summary for 1.1.3.47 extracted from

  • Gandomkar, S.; Jost, E.; Loidolt, D.; Swoboda, A.; Pickl, M.; Elaily, W.; Daniel, B.; Fraaije, M.; Macheroux, P.; Kroutil, W.
    Biocatalytic enantioselective oxidation of sec-allylic alcohols with flavin-dependent oxidases (2019), Adv. Synth. Catal., 361, 5264-5271 .
    View publication on PubMedView publication on EuropePMC

Application

Application Comment Organism
synthesis enantioselective oxidation of sec-allylic alcohols using variants of the berberine bridge enzyme analogue from Arabidopsis thaliana (AtBBE15) and the 5-(hydroxymethyl)furfural oxidase (HMFO) and its variants V465T, V465S, V465T/W466H and V367R/W466F. The enantioselectivity can be tuned by applying either pressure or by the addition of cosolvents Methylovorus sp. MP688

Cloned(Commentary)

Cloned (Comment) Organism
expression in Escherichia coli Methylovorus sp. MP688

Protein Variants

Protein Variants Comment Organism
V367R/W466F significant improvement of conversion rate Methylovorus sp. MP688
V465S significant improvement of conversion rate Methylovorus sp. MP688
V465T significant improvement of conversion rate and enantioselectivity with sec-allylic alcohols Methylovorus sp. MP688
V465T/W466H significant improvement of conversion rate Methylovorus sp. MP688

Organic Solvent Stability

Organic Solvent Comment Organism
additional information the enantioselectivity of the reaction with sec-allylic alcohols can be tuned by applying either pressure or by the addition of cosolvents sucgh as DMSO, isooctane, glycerol, n-heptane, methynol, ethanol, acetone, DMF Methylovorus sp. MP688

Organism

Organism UniProt Comment Textmining
Methylovorus sp. MP688 E4QP00
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2R,3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-ol + O2 4% conversion, 2% enantiomeric excess Methylovorus sp. MP688 (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one + H2O2
-
?
(2R,3E)-4-(4-chlorophenyl)but-3-en-2-ol + O2 10% conversion, 10% enantiomeric excess Methylovorus sp. MP688 (3E)-4-(4-chlorophenyl)but-3-en-2-one + H2O2
-
?
(2R,3E)-4-(4-methylphenyl)but-3-en-2-ol + O2 13% conversion, 14% enantiomeric excess Methylovorus sp. MP688 (3E)-4-(4-methylphenyl)but-3-en-2-one + H2O2
-
?
(2R,3E)-4-phenylbut-3-en-2-ol + O2 29% conversion, 25% enantiomeric excess Methylovorus sp. MP688 (3E)-4-phenylbut-3-en-2-one + H2O2
-
?
(2R,3E)-oct-3-en-2-ol + O2 16% conversion, 19% enantiomeric excess Methylovorus sp. MP688 (3E)-oct-3-en-2-one + H2O2
-
?
additional information for sec-allylic alcohol substrates, exclusively oxidation of the allylic alcohol to the alpha,beta-unsaturated ketone is observed. The reaction is enantioselective for the R-enantiomer Methylovorus sp. MP688 ?
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Synonyms

Synonyms Comment Organism
HMFO
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Methylovorus sp. MP688

Cofactor

Cofactor Comment Organism Structure
FAD
-
Methylovorus sp. MP688