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Literature summary extracted from

  • Darsandhari, S.; Dhakal, D.; Shrestha, B.; Parajuli, P.; Seo, J.H.; Kim, T.S.; Sohng, J.K.
    Characterization of regioselective flavonoid O-methyltransferase from the Streptomyces sp. KCTC 0041BP (2018), Enzyme Microb. Technol., 113, 29-36 .
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.1.1.231 gene gerMIII, GerMIII is present on the biosynthetic gene cluster of dihydrochalcomycin, a macrolide antibiotic that is produced by the Streptomyces sp. KCTC 0041BP, sequence comparisons and phylogenetic analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Streptomyces sp. KCTC 0041BP

Inhibitors

EC Number Inhibitors Comment Organism Structure
2.1.1.231 Co2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP
2.1.1.231 Cu2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP
2.1.1.231 EDTA
-
 Streptomyces sp. KCTC 0041BP
2.1.1.231 Fe2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP
2.1.1.231 Mn2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP
2.1.1.231 Ni2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP
2.1.1.231 Pb2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP
2.1.1.231 Zn2+ complete inhibition at 20 mM Streptomyces sp. KCTC 0041BP

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.1.1.231 additional information
-
 additional information Michaelis-Menten kinetic analysis Streptomyces sp. KCTC 0041BP
2.1.1.231 0.00183
-
 S-adenosyl-L-methionine pH 7.5, 37°C Streptomyces sp. KCTC 0041BP
2.1.1.231 0.163
-
 quercetin pH 7.5, 37°C Streptomyces sp. KCTC 0041BP

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.1.1.231 Mg2+ required, 2fold activation at 20 mM. Mg2+ comprises an octahedral coordination environment that is suitable for the two aspartic-acid residues Asp279 and Asp308 and two water molecules Streptomyces sp. KCTC 0041BP

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.1.1.231 S-adenosyl-L-methionine + quercetin Streptomyces sp. KCTC 0041BP
-
 S-adenosyl-L-homocysteine + tamarixetin
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.1.1.231 Streptomyces sp. KCTC 0041BP Q331Q6
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.1.1.231 recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by cobalt affinity chromatography Streptomyces sp. KCTC 0041BP

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.1.1.231 additional information among the flavonoids, quercetin is the most favorable substrate, followed by luteolin, myricetin, quercetin glucoside, and fisetin, while only a single product is formed in each case. Product identification by mass-spectrometry and NMR spectrometric analysis. Susbtrate specificity, overview. Mechanistic overview of the regiospecific modification, a double bond between the C2 and the C3 and a single-ring-appended conjugate-hydroxyl group are crucial for the favorable enzymatic conversions of the GerMIII catalysis, modeling and molecular docking. Of all of the anthraquinones that are tested, only alizarin is methylated by the GerMIII at a detectable amount, whereas the methylation of all of the other remaining compounds is not evident. The common feature among the GerMIII substrates is the existence of two neighboring hydroxyl groups in the presence of a double bond between the C2 and the C3, as found in the quercetin, luteolin, myricetin, fisetin, and quercetin glucoside. GerMIII does not methylate many substrates including the close flavonoid relative catechin, which lacks the double bond between the C2 and the C3 Streptomyces sp. KCTC 0041BP ?
-
-
2.1.1.231 S-adenosyl-L-methionine + alizarin
-
 Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + methylalizarin
-
 ?
2.1.1.231 S-adenosyl-L-methionine + fisetin 8% activity with fisetin compared to quercetin Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + 4'-methoxyfisetin
-
 ?
2.1.1.231 S-adenosyl-L-methionine + luteolin 67% activity with luteolin compared to quercetin Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + 4'-methoxyluteolin
-
 ?
2.1.1.231 S-adenosyl-L-methionine + myricetin 20% activity with luteolin compared to quercetin Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + 4'-methoxymyricetin
-
 ?
2.1.1.231 S-adenosyl-L-methionine + quercetin best substrate, 85% conversion at 2 mM substrate Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + 4'-methoxyquercetin
-
 ?
2.1.1.231 S-adenosyl-L-methionine + quercetin
-
 Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + tamarixetin
-
 ?
2.1.1.231 S-adenosyl-L-methionine + quercetin 3-O-beta-D-glucoside 16% activity with quercetin glucoside compared to quercetin Streptomyces sp. KCTC 0041BP S-adenosyl-L-homocysteine + 4'-methoxyquercetin 3-O-beta-D-glucoside
-
 ?

Subunits

EC Number Subunits Comment Organism
2.1.1.231 ? x * 44000, about, sequence calculation Streptomyces sp. KCTC 0041BP
2.1.1.231 More three-dimensional enzyme structure analysis and modelling, overview Streptomyces sp. KCTC 0041BP

Synonyms

EC Number Synonyms Comment Organism
2.1.1.231 4'OMT
-
 Streptomyces sp. KCTC 0041BP
2.1.1.231 GerMIII
-
 Streptomyces sp. KCTC 0041BP
2.1.1.231 O-methyltransferase
-
 Streptomyces sp. KCTC 0041BP
2.1.1.231 OMT
-
 Streptomyces sp. KCTC 0041BP
2.1.1.231 regiospecific flavonoid 4'OMT
-
 Streptomyces sp. KCTC 0041BP

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.1.1.231 37
-
-
 Streptomyces sp. KCTC 0041BP

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.1.1.231 0.027
-
 S-adenosyl-L-methionine pH 7.5, 37°C Streptomyces sp. KCTC 0041BP
2.1.1.231 0.027
-
 quercetin pH 7.5, 37°C Streptomyces sp. KCTC 0041BP

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.1.1.231 7.5
-
-
 Streptomyces sp. KCTC 0041BP

Cofactor

EC Number Cofactor Comment Organism Structure
2.1.1.231 S-adenosyl-L-methionine
-
 Streptomyces sp. KCTC 0041BP

General Information

EC Number General Information Comment Organism
2.1.1.231 evolution GerMIII is present on the biosynthetic gene cluster of dihydrochalcomycin, a macrolide antibiotic that is produced by the Streptomyces sp. KCTC 0041BP. Based on its dependency on the metallic cofactor requirement for its reaction, the enzyme resembles the Class-II plant OMTs Streptomyces sp. KCTC 0041BP
2.1.1.231 additional information a double bond between the C2 and the C3 and a single-ring-appended conjugate-hydroxyl group are crucial for the favorable enzymatic conversions of the GerMIII catalysis, modeling and molecular docking Streptomyces sp. KCTC 0041BP
2.1.1.231 physiological function the methylation at the 4'-hydroxyl group of the B-ring of flavonoids confers a structural constraint for autooxidation, importance of the regiospecific 4'-OMT Streptomyces sp. KCTC 0041BP

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.1.1.231 0.166
-
 quercetin pH 7.5, 37°C Streptomyces sp. KCTC 0041BP
2.1.1.231 14.75
-
 S-adenosyl-L-methionine pH 7.5, 37°C Streptomyces sp. KCTC 0041BP