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Literature summary for 1.1.1.4 extracted from

  • Muschallik, L.; Molinnus, D.; Jablonski, M.; Kipp, C.; Bongaerts, J.; Pohl, M.; Wagner, T.; Schoening, M.; Selmer, T.; Siegert, P.
    Synthesis of alpha-hydroxy ketones and vicinal (R,R)-diols by Bacillus clausii DSM 8716T butanediol dehydrogenase (2020), RSC Adv., 10, 12206-12216 .
No PubMed abstract available

Cloned(Commentary)

Cloned (Comment) Organism
gene bdhA, recombinant expression of N-terminally StrepII-tagged enzyme in Escherichia coli strain BL21(DE3) Alkalihalobacillus clausii

Protein Variants

Protein Variants Comment Organism
additional information the biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated Alkalihalobacillus clausii

Metals/Ions

Metals/Ions Comment Organism Structure
Mn2+ 1 mM Mn2+ increases BcBDH's activity in biotransformations Alkalihalobacillus clausii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(2R,3R)-butane-2,3-diol + NAD+ Alkalihalobacillus clausii
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(3R)-acetoin + NADH + H+
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r
(2R,3R)-butane-2,3-diol + NAD+ Alkalihalobacillus clausii DSM 8716T
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(3R)-acetoin + NADH + H+
-
r

Organism

Organism UniProt Comment Textmining
Alkalihalobacillus clausii A0A223LRZ7
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Alkalihalobacillus clausii DSM 8716T A0A223LRZ7
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-

Purification (Commentary)

Purification (Comment) Organism
recombinant N-terminally StrepII-tagged enzyme from Escherichia coli strain BL21(DE3) by affinity chromatography Alkalihalobacillus clausii

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2R,3R)-butane-2,3-diol + NAD+
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Alkalihalobacillus clausii (3R)-acetoin + NADH + H+
-
r
(2R,3R)-butane-2,3-diol + NAD+
-
Alkalihalobacillus clausii DSM 8716T (3R)-acetoin + NADH + H+
-
r
2,3-hexanedione + NADH + H+ small amounts of (2R)-2-hydroxy-3-hexanone are produced as by-product Alkalihalobacillus clausii (3R)-3-hydroxy-2-hexanone + NAD+
-
r
2,3-hexanedione + NADH + H+ small amounts of (2R)-2-hydroxy-3-hexanone are produced as by-product Alkalihalobacillus clausii DSM 8716T (3R)-3-hydroxy-2-hexanone + NAD+
-
r
2,3-pentanedione + NADH + H+ small amounts of 2,3-pentanediol are produced as by-product Alkalihalobacillus clausii 3-hydroxy-2-pentanone + NAD+
-
r
2,3-pentanedione + NADH + H+ small amounts of 2,3-pentanediol are produced as by-product Alkalihalobacillus clausii DSM 8716T 3-hydroxy-2-pentanone + NAD+
-
r
3,4-hexanedione + 2 NADH + 2 H+
-
Alkalihalobacillus clausii (3R,4R)-3,4-hexanediol + 2 NAD+
-
r
5-methyl-2,3-hexanedione + NADH + H+ small amounts of 5-methyl-2-hydroxy-3-hexanone and traces of (3S)-5-methyl-3-hydroxy-2-hexanone are produced as by-products Alkalihalobacillus clausii (3R)-5-methyl-3-hydroxy-2-hexanone + NAD+
-
r
5-methyl-2,3-hexanedione + NADH + H+ small amounts of 5-methyl-2-hydroxy-3-hexanone and traces of (3S)-5-methyl-3-hydroxy-2-hexanone are produced as by-products Alkalihalobacillus clausii DSM 8716T (3R)-5-methyl-3-hydroxy-2-hexanone + NAD+
-
r
additional information substrate specificity analysis, overview. Enzyme BcBDH catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione, and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. The biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated. Stereoselectivity and conversion is analyzed by carrying out the reduction reaction of selected diketones and alpha-hydroxyketones Alkalihalobacillus clausii ?
-
-
additional information substrate specificity analysis, overview. Enzyme BcBDH catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione, and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. The biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated. Stereoselectivity and conversion is analyzed by carrying out the reduction reaction of selected diketones and alpha-hydroxyketones Alkalihalobacillus clausii DSM 8716T ?
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-

Synonyms

Synonyms Comment Organism
(R,R)-butane-2,3-diol dehydrogenase
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Alkalihalobacillus clausii
BcBDH
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Alkalihalobacillus clausii
BdhA
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Alkalihalobacillus clausii
butanediol dehydrogenase
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Alkalihalobacillus clausii
R-selective 2,3-butanediol dehydrogenase
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Alkalihalobacillus clausii

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Alkalihalobacillus clausii

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.8
-
assay at Alkalihalobacillus clausii

General Information

General Information Comment Organism
evolution the R-selective 2,3-butanediol dehydrogenase from Bacillus clausii strain DSM 8716 (BcBDH) belongs to the metal-dependent medium chain dehydrogenases/reductases family (MDR) Alkalihalobacillus clausii