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Literature summary for 1.1.1.B20 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
Search for more literature for 1.1.1.B20

Cloned(Commentary)

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

Inhibitors

Inhibitors Comment Organism Structure
NADH subsrate inhibition in acetoin reduction at concentrations above 0.3 mM Serratia marcescens

KM Value [mM]

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

Metals/Ions

Metals/Ions Comment Organism Structure
additional information the enzyme is metal-independent Serratia marcescens

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Serratia marcescens H9XP47
-
-
Serratia marcescens CECT 977 H9XP47
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(2R,3S)-butane-2,3-diol + NAD+
-
 Serratia marcescens (3R)-acetoin + NADH + H+
-
 r
(2R,3S)-butane-2,3-diol + NAD+
-
 Serratia marcescens CECT 977 (3R)-acetoin + NADH + H+
-
 r
(3R)-acetoin + NADH + H+
-
 Serratia marcescens (2R,3S)-butane-2,3-diol + NAD+
-
 r
(3R)-acetoin + NADH + H+
-
 Serratia marcescens CECT 977 (2R,3S)-butane-2,3-diol + NAD+
-
 r
1,2-cyclohexanedione + NADH + H+
-
 Serratia marcescens (S,S)-1,2-cyclohexanediol + NAD+
-
 ?
1,2-cyclohexanedione + NADH + H+
-
 Serratia marcescens CECT 977 (S,S)-1,2-cyclohexanediol + NAD+
-
 ?
1-phenyl-1,2-propanedione + NADH + H+
-
 Serratia marcescens (S)-2-hydroxy-1-phenylpropan-1-one + NAD+
-
 ?
1-phenyl-1,2-propanedione + NADH + H+
-
 Serratia marcescens CECT 977 (S)-2-hydroxy-1-phenylpropan-1-one + NAD+
-
 ?
2,3-heptanedione + NADH + H+
-
 Serratia marcescens 3-hydroxy-2-heptanone + NAD+
-
 ?
2,3-hexanedione + NADH + H+
-
 Serratia marcescens (S)-3-hydroxy-2-hexanone + NAD+
-
 ?
2,3-pentanedione + NADH + H+
-
 Serratia marcescens (3S)-3-hydroxy-2-pentanone + NAD+
-
 ?
3,4-hexanedione + NADH + H+
-
 Serratia marcescens (3S,4S)-3,4-hexanediol + NAD+
-
 ?
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 ?
-
-
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

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

Synonyms

Synonyms Comment Organism
2,3-butanediol dehydrogenase
-
 Serratia marcescens
budC
-
 Serratia marcescens
meso-2,3-butanediol dehydrogenase
-
 Serratia marcescens

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Serratia marcescens

Turnover Number [1/s]

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

pH Optimum

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

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Serratia marcescens
NADH NADH-dependent enzyme Serratia marcescens

General Information

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

kcat/KM [mM/s]

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