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Literature summary extracted from

  • Medici, R.; Stammes, H.; Kwakernaak, S.; Otten, L.; Hanefeld, U.
    Assessing the stereoselectivity of Serratia marcescens CECT 977 2,3-butanediol dehydrogenase (2017), Catal. Sci. Technol., 7, 1831-1837 .
No PubMed abstract available

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.B20 gene budC, recombinant expression of N-terminally His-tagged enzyme in Escherichia coli strain BL21 Star (DE3) Serratia marcescens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.B20 NADH subsrate inhibition in acetoin reduction at concentrations above 0.3 mM Serratia marcescens

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.B20 3.1
-
 (3R)-acetoin pH 7.0, 37°C Serratia marcescens
1.1.1.B20 6.9
-
 (2R,3S)-butane-2,3-diol pH 7.0, 37°C Serratia marcescens

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.1.1.B20 additional information the enzyme is metal-independent Serratia marcescens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.B20 (2R,3S)-butane-2,3-diol + NAD+ Serratia marcescens
-
 (3R)-acetoin + NADH + H+
-
 r
1.1.1.B20 (2R,3S)-butane-2,3-diol + NAD+ Serratia marcescens CECT 977
-
 (3R)-acetoin + NADH + H+
-
 r

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.B20 Serratia marcescens H9XP47
-
-
1.1.1.B20 Serratia marcescens CECT 977 H9XP47
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.B20 recombinant N-terminally His-tagged enzyme from Escherichia coli strain BL21 Star (DE3) by nickel affinity chromatography Serratia marcescens

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.B20 (2R,3S)-butane-2,3-diol + NAD+
-
 Serratia marcescens (3R)-acetoin + NADH + H+
-
 r
1.1.1.B20 (2R,3S)-butane-2,3-diol + NAD+
-
 Serratia marcescens CECT 977 (3R)-acetoin + NADH + H+
-
 r
1.1.1.B20 (3R)-acetoin + NADH + H+
-
 Serratia marcescens (2R,3S)-butane-2,3-diol + NAD+
-
 r
1.1.1.B20 (3R)-acetoin + NADH + H+
-
 Serratia marcescens CECT 977 (2R,3S)-butane-2,3-diol + NAD+
-
 r
1.1.1.B20 1,2-cyclohexanedione + NADH + H+
-
 Serratia marcescens (S,S)-1,2-cyclohexanediol + NAD+
-
 ?
1.1.1.B20 1,2-cyclohexanedione + NADH + H+
-
 Serratia marcescens CECT 977 (S,S)-1,2-cyclohexanediol + NAD+
-
 ?
1.1.1.B20 1-phenyl-1,2-propanedione + NADH + H+
-
 Serratia marcescens (S)-2-hydroxy-1-phenylpropan-1-one + NAD+
-
 ?
1.1.1.B20 1-phenyl-1,2-propanedione + NADH + H+
-
 Serratia marcescens CECT 977 (S)-2-hydroxy-1-phenylpropan-1-one + NAD+
-
 ?
1.1.1.B20 2,3-heptanedione + NADH + H+
-
 Serratia marcescens 3-hydroxy-2-heptanone + NAD+
-
 ?
1.1.1.B20 2,3-hexanedione + NADH + H+
-
 Serratia marcescens (S)-3-hydroxy-2-hexanone + NAD+
-
 ?
1.1.1.B20 2,3-pentanedione + NADH + H+
-
 Serratia marcescens (3S)-3-hydroxy-2-pentanone + NAD+
-
 ?
1.1.1.B20 3,4-hexanedione + NADH + H+
-
 Serratia marcescens (3S,4S)-3,4-hexanediol + NAD+
-
 ?
1.1.1.B20 additional information 2,3-butanediol dehydrogenase (BudC) catalyses the selective asymmetric reductions of prochiral alpha-diketones to the corresponding alpha-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones, and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions. Substrate specificity and stereoselectivity, overview. In the reductive reaction diacetyl is the preferred substrate of BudC over acetoin, while only meso-2,3-butanediol oxidation is catalysed by the enzyme under the conditions assessed. No activity with (2S,3S)-butane-2,3-diol and (2R,3R)-butane-2,3-diol. BudC is S-selective for the reduction of diacetyl yielding (S,S)-2,3-butanediol ((S,S)-2,3-BDO), rac-acetoin is reduced to both meso-2,3-BDO and (S,S)-2,3-BDO. Here (R)-acetoin is the preferred substrate and 15% (S)-acetoin remains unconverted after 24 h. Thus, BudC shows a stereo-preference consistent with meso-2,3-butanediol dehydrogenases with respect to acetoin. No activity with R-benzoin, rac-benzoin, benzil, acetone, 2,4-pentanediol, 1,3-butanediol, ethanol, and 2-propanol Serratia marcescens ?
-
-
1.1.1.B20 additional information 2,3-butanediol dehydrogenase (BudC) catalyses the selective asymmetric reductions of prochiral alpha-diketones to the corresponding alpha-hydroxy ketones and diols. BudC is highly active towards structurally diverse diketones in combination with nicotinamide cofactor regeneration systems. Aliphatic diketones, cyclic diketones, and alkyl phenyl diketones are well accepted, whereas their derivatives possessing two bulky groups are not converted. In the reverse reaction vicinal diols are preferred over other substrates with hydroxy/keto groups in non-vicinal positions. Substrate specificity and stereoselectivity, overview. In the reductive reaction diacetyl is the preferred substrate of BudC over acetoin, while only meso-2,3-butanediol oxidation is catalysed by the enzyme under the conditions assessed. No activity with (2S,3S)-butane-2,3-diol and (2R,3R)-butane-2,3-diol. BudC is S-selective for the reduction of diacetyl yielding (S,S)-2,3-butanediol ((S,S)-2,3-BDO), rac-acetoin is reduced to both meso-2,3-BDO and (S,S)-2,3-BDO. Here (R)-acetoin is the preferred substrate and 15% (S)-acetoin remains unconverted after 24 h. Thus, BudC shows a stereo-preference consistent with meso-2,3-butanediol dehydrogenases with respect to acetoin. No activity with R-benzoin, rac-benzoin, benzil, acetone, 2,4-pentanediol, 1,3-butanediol, ethanol, and 2-propanol Serratia marcescens CECT 977 ?
-
-

Subunits

EC Number Subunits Comment Organism
1.1.1.B20 ? x * 28400, about, sequence calculation, x * 28000, recombinant His-tagged enzyme, SDS-PAGE Serratia marcescens

Synonyms

EC Number Synonyms Comment Organism
1.1.1.B20 2,3-butanediol dehydrogenase
-
 Serratia marcescens
1.1.1.B20 budC
-
 Serratia marcescens
1.1.1.B20 meso-2,3-butanediol dehydrogenase
-
 Serratia marcescens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.B20 37
-
 assay at Serratia marcescens

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.1.1.B20 66.6
-
 (2R,3S)-butane-2,3-diol pH 7.0, 37°C Serratia marcescens
1.1.1.B20 195
-
 (3R)-acetoin pH 7.0, 37°C Serratia marcescens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.B20 5
-
 acetoin reduction Serratia marcescens
1.1.1.B20 7
-
 assay at, (2R,3S)-butane-2,3-diol oxidation Serratia marcescens

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.B20 NAD+
-
 Serratia marcescens
1.1.1.B20 NADH NADH-dependent enzyme Serratia marcescens

General Information

EC Number General Information Comment Organism
1.1.1.B20 evolution the enzyme belongs to the NADH-dependent metal-independent short-chain dehydrogenases/reductase (SDR) family of oxidoreductases Serratia marcescens

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.1.1.B20 9.65
-
 (2R,3S)-butane-2,3-diol pH 7.0, 37°C Serratia marcescens
1.1.1.B20 62.9
-
 (3R)-acetoin pH 7.0, 37°C Serratia marcescens