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Literature summary extracted from

  • Wang, Z.; Song, Q.; Yu, M.; Wang, Y.; Xiong, B.; Zhang, Y.; Zheng, J.; Ying, X.
    Characterization of a stereospecific acetoin(diacetyl) reductase from Rhodococcus erythropolis WZ010 and its application for the synthesis of (2S,3S)-2,3-butanediol (2014), Appl. Microbiol. Biotechnol., 98, 641-650.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.1.1.304 DMSO DMSO at a final concentration of 30% v/v added into the assay mixture, increases the activity up to 120% of the control enzyme activity Rhodococcus erythropolis

Application

EC Number Application Comment Organism
1.1.1.76 synthesis the key enzymes in the microbial production of 2,3-butanediol Rhodococcus erythropolis
1.1.1.304 synthesis acetoin(diacetyl) reductase, i.e. 2,3-butanediol dehydrogenase, is one of the key enzymes in the microbial production of 2,3-butanediol, a platform with extensive industrial applications in the production of plastics, printing inks, perfumes, fumigants, spandex, moistening and softening agents, plasticizers, and pharmaceutical carrier Rhodococcus erythropolis

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.1.1.76 recombinant overexpression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Rhodococcus erythropolis
1.1.1.304 gene adr, DNA and amino acid sequence determination and analysis, sequence comparison Rhodococcus erythropolis
1.1.1.304 gene adr, DNA and amino acid sequence determination and analysis, sequence comparison, expression of His-tagged enzyme in Escherichia coli Rhodococcus erythropolis

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.1.1.304 Al3+
-
 Rhodococcus erythropolis
1.1.1.304 Fe2+ inhibits 91.6% at 2 mM Rhodococcus erythropolis
1.1.1.304 Zn2+ inhibits 94.6% at 2 mM Rhodococcus erythropolis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.1.1.304 additional information
-
 additional information Michaelis-Menten-type kinetics Rhodococcus erythropolis

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.1.1.304 K+ activates by 201.6 to 265.6% at 2 mM Rhodococcus erythropolis
1.1.1.304 Mn2+ activates by 201.6 to 265.6% at 2 mM Rhodococcus erythropolis
1.1.1.304 additional information addition of EDTA or the cations at 1 mM, such as Na+, K+, Mn2+, Mg2+, and Ca2+, have no significant effect on the activity of ReADR Rhodococcus erythropolis
1.1.1.304 Na+ activates by 201.6 to 265.6% at 2 mM Rhodococcus erythropolis

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.1.1.76 26864
-
 2 * 26864, sequence calculation Rhodococcus erythropolis
1.1.1.304 26864
-
 2 * 26864, sequence calculation Rhodococcus erythropolis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.76 (2S,3S)-butane-2,3-diol + NAD+ Rhodococcus erythropolis the enzyme displayed absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. Physiological role in favor of (2S,3S)-2,3-butanediol formation (S)-acetoin + NADH + H+
-
 r
1.1.1.304 diacetyl + NADH + H+ Rhodococcus erythropolis
-
 (R)-acetoin + NAD+
-
 r
1.1.1.304 diacetyl + NADH + H+ Rhodococcus erythropolis
-
 (S)-acetoin + NAD+
-
 r
1.1.1.304 diacetyl + NADH + H+ Rhodococcus erythropolis PR4
-
 (R)-acetoin + NAD+
-
 r
1.1.1.304 diacetyl + NADH + H+ Rhodococcus erythropolis WZ010
-
 (S)-acetoin + NAD+
-
 r
1.1.1.304 additional information Rhodococcus erythropolis Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation. ?
-
 ?
1.1.1.304 additional information Rhodococcus erythropolis WZ010 Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation. ?
-
 ?

Organic Solvent Stability

EC Number Organic Solvent Comment Organism
1.1.1.76 DMSO the enzyme exhibits remarkable tolerance to dimethyl sulfoxide and retains 53.6% of the initial activity after 4 h incubation with 30% v/v DMSO Rhodococcus erythropolis
1.1.1.304 DMSO the enzyme retains 53.6% of the initial activity after 4 h incubation with 30% v/v DMSO at 4°C Rhodococcus erythropolis

Organism

EC Number Organism UniProt Comment Textmining
1.1.1.76 Rhodococcus erythropolis M4N626
-
-
1.1.1.76 Rhodococcus erythropolis WZ010 M4N626
-
-
1.1.1.304 Rhodococcus erythropolis
-
 gene adr
-
1.1.1.304 Rhodococcus erythropolis C0ZPN9 gene adr
-
1.1.1.304 Rhodococcus erythropolis PR4 C0ZPN9 gene adr
-
1.1.1.304 Rhodococcus erythropolis WZ010
-
 gene adr
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.1.1.76 recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography Rhodococcus erythropolis
1.1.1.304 recombinant His-tagged enzyme from Escherichia coli by nickel affinity chromatography Rhodococcus erythropolis

Specific Activity [micromol/min/mg]

EC Number Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
1.1.1.76 269
-
 purified recombinant enzyme, (2S,3S)-2,3-butanediol oxidation, pH 9.5, 25°C Rhodococcus erythropolis
1.1.1.76 8519
-
 purified recombinant enzyme, diacetyl reduction, pH 7.0, 30°C Rhodococcus erythropolis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.76 (2S,3S)-butane-2,3-diol + NAD+ the enzyme displayed absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. Physiological role in favor of (2S,3S)-2,3-butanediol formation Rhodococcus erythropolis (S)-acetoin + NADH + H+
-
 r
1.1.1.76 (2S,3S)-butane-2,3-diol + NAD+ the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. Under the optimized conditions, the activity of diacetyl reduction is 11.9fold higher than that of (2S,3S)-2,3-butanediol oxidation Rhodococcus erythropolis (S)-acetoin + NADH + H+
-
 r
1.1.1.76 (S)-1-phenylethanol + NAD+
-
 Rhodococcus erythropolis acetophenone + NADH + H+
-
 r
1.1.1.76 1,2-propanediol + NAD+
-
 Rhodococcus erythropolis ? + NADH + H+
-
 ?
1.1.1.76 1-butanol + NAD+
-
 Rhodococcus erythropolis butanal + NADH + H+
-
 ?
1.1.1.76 1-butanol + NAD+
-
 Rhodococcus erythropolis WZ010 butanal + NADH + H+
-
 ?
1.1.1.76 1-phenylpropanol + NAD+
-
 Rhodococcus erythropolis 1-phenylpropan-1-one + NADH + H+
-
 ?
1.1.1.76 2,2,2-trifluoroacetophenone + NADH + H+
-
 Rhodococcus erythropolis ? + NAD+
-
 ?
1.1.1.76 2-butanol + NAD+
-
 Rhodococcus erythropolis 2-butanone + NADH + H+
-
 ?
1.1.1.76 2-butanol + NAD+
-
 Rhodococcus erythropolis WZ010 2-butanone + NADH + H+
-
 ?
1.1.1.76 2-pentanol + NAD+
-
 Rhodococcus erythropolis 2-pentanone + NADH + H+
-
 ?
1.1.1.76 2-pentanol + NAD+
-
 Rhodococcus erythropolis WZ010 2-pentanone + NADH + H+
-
 ?
1.1.1.76 cyclohexanol + NAD+
-
 Rhodococcus erythropolis cyclohexanone + NADH + H+
-
 ?
1.1.1.76 cyclohexanol + NAD+
-
 Rhodococcus erythropolis WZ010 cyclohexanone + NADH + H+
-
 ?
1.1.1.76 ethyl pyruvate + NADH + H+
-
 Rhodococcus erythropolis ? + NAD+
-
 ?
1.1.1.76 isopropanol + NAD+
-
 Rhodococcus erythropolis isopropanal + NADH + H+
-
 ?
1.1.1.76 additional information the enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones, overview. No activity with 4-chloroacetophenone, (R)-1-phenylethanol, and (2R,3R)-2,3-butanediol, poor activity with 3-methyl-2-acetophenone, 4-bromoacetophenone, 2-bromoacetophenone, benzaldehyde, and isophorone Rhodococcus erythropolis ?
-
 ?
1.1.1.76 additional information the enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones, overview. No activity with 4-chloroacetophenone, (R)-1-phenylethanol, and (2R,3R)-2,3-butanediol, poor activity with 3-methyl-2-acetophenone, 4-bromoacetophenone, 2-bromoacetophenone, benzaldehyde, and isophorone Rhodococcus erythropolis WZ010 ?
-
 ?
1.1.1.304 diacetyl + NADH + H+
-
 Rhodococcus erythropolis (R)-acetoin + NAD+
-
 r
1.1.1.304 diacetyl + NADH + H+
-
 Rhodococcus erythropolis PR4 (R)-acetoin + NAD+
-
 r
1.1.1.304 diacetyl + NADH + H+
-
 Rhodococcus erythropolis (S)-acetoin + NAD+
-
 r
1.1.1.304 diacetyl + NADH + H+
-
 Rhodococcus erythropolis WZ010 (S)-acetoin + NAD+
-
 r
1.1.1.304 additional information Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation. Rhodococcus erythropolis ?
-
 ?
1.1.1.304 additional information the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones Rhodococcus erythropolis ?
-
 ?
1.1.1.304 additional information Rhodococcus erythropolis WZ010 is capable of producing optically pure (2S,3S)-2,3-butanediol in alcoholic fermentation. Rhodococcus erythropolis WZ010 ?
-
 ?
1.1.1.304 additional information the enzyme displays absolute stereospecificity in the reduction of diacetyl to (2S,3S)-2,3-butanediol via (S)-acetoin. The enzyme shows higher catalytic efficiency for (S)-1-phenylethanol oxidation than that for acetophenone reduction. ReADR-catalyzed asymmetric reduction of diacetyl is coupled with stereoselective oxidation of 1-phenylethanol, which simultaneously forms both (2S,3S)-2,3-butanediol and (R)-1-phenylethanol in great conversions and enantiomeric excess values.The enzyme accepts a broad range of substrates including aliphatic and aryl alcohols, aldehydes, and ketones Rhodococcus erythropolis WZ010 ?
-
 ?

Subunits

EC Number Subunits Comment Organism
1.1.1.76 homodimer 2 * 26864, sequence calculation Rhodococcus erythropolis
1.1.1.304 homodimer 2 * 26864, sequence calculation Rhodococcus erythropolis

Synonyms

EC Number Synonyms Comment Organism
1.1.1.76 2,3-butanediol dehydrogenase
-
 Rhodococcus erythropolis
1.1.1.76 acetoin(diacetyl) reductase
-
 Rhodococcus erythropolis
1.1.1.76 AdR
-
 Rhodococcus erythropolis
1.1.1.304 acetoin(diacetyl) reductase
-
 Rhodococcus erythropolis
1.1.1.304 AdR
-
 Rhodococcus erythropolis
1.1.1.304 ReADR
-
 Rhodococcus erythropolis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.1.1.76 25
-
 (2S,3S)-2,3-butanediol oxidation Rhodococcus erythropolis
1.1.1.76 30
-
 diacetyl reduction Rhodococcus erythropolis
1.1.1.304 30
-
 diacetyl reduction Rhodococcus erythropolis

Temperature Range [°C]

EC Number Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
1.1.1.76 10 50 activity range Rhodococcus erythropolis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.1.1.76 7
-
 diacetyl reduction Rhodococcus erythropolis
1.1.1.76 9.5
-
 (2S,3S)-2,3-butanediol oxidation Rhodococcus erythropolis
1.1.1.304 7
-
 diacetyl reduction Rhodococcus erythropolis

pH Range

EC Number pH Minimum pH Maximum Comment Organism
1.1.1.76 6.1 11 activity range Rhodococcus erythropolis

Cofactor

EC Number Cofactor Comment Organism Structure
1.1.1.76 NAD+ coenzyme binding motif T11G12XXXG16XG18 is conserved in the N-terminal region Rhodococcus erythropolis
1.1.1.304 NAD+
-
 Rhodococcus erythropolis
1.1.1.304 NADH
-
 Rhodococcus erythropolis

General Information

EC Number General Information Comment Organism
1.1.1.76 evolution the enzyme belongs to the family of the short-chain dehydrogenase/reductases Rhodococcus erythropolis
1.1.1.304 evolution the enzyme belongs to the family of the short-chain dehydrogenase/reductases Rhodococcus erythropolis
1.1.1.304 metabolism acetoin(diacetyl) reductase, also known as 2,3-butanediol dehydrogenase, is one of the key enzymes in the microbial production of 2,3-butanediol Rhodococcus erythropolis

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
1.1.1.304 8.519
-
 NADH pH 7.0, 30°C, recombinant enzyme Rhodococcus erythropolis