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Literature summary extracted from

  • Aldrich, C.C.; Beck, B.J.; Fecik, R.A.; Sherman, D.H.
    Biochemical investigation of pikromycin biosynthesis employing native penta- and hexaketide chain elongation intermediates (2005), J. Am. Chem. Soc., 127, 8441-8452.
    View publication on PubMed

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.3.1.240 overexpression of polyketide synthase PikAIII, and polyketide synthase PikAIV in Escherichia coli Streptomyces venezuelae

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
2.3.1.239 0.25
-
 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate pH 7.2, 30°C, KM-value for activity with the polyketide synthase PikAIII/polyketide synthase PikAIV complex in formation of 10-deoxymethynolide Streptomyces venezuelae
2.3.1.240 0.41
-
 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate pH 7.2, 30°C, Km-valkue for activity with the polyketide synthase PikAIII/polyketide synthase PikAIV complex in formation of narbonolide Streptomyces venezuelae

Organism

EC Number Organism UniProt Comment Textmining
2.3.1.239 Streptomyces venezuelae Q9ZGI5 and Q9ZGI4 and Q9ZGI3 and Q9ZGI2 and Q9ZGI1 Q9ZGI5: type I polyketide synthase PikAI, Q9ZGI4: type I polyketide synthase PikAII, Q9ZGI3: type I polyketide synthase PikAIII, Q9ZGI2: type I polyketide synthase PikAIV, Q9ZGI1: thioesterase II PikAV. Multifunctional, modular enzyme
-
2.3.1.240 Streptomyces venezuelae Q9ZGI5 and Q9ZGI4 and Q9ZGI3 and Q9ZGI2 and Q9ZGI1 Q9ZGI5: type I polyketide synthase PikAI, Q9ZGI4: type I polyketide synthase PikAII, Q9ZGI3: type I polyketide synthase PikAIII, Q9ZGI2: type I polyketide synthase PikAIV, Q9ZGI1: thioesterase II PikAV. Multifunctional, modular enzyme
-
2.3.1.240 Streptomyces venezuelae ATCC 15439 Q9ZGI5 and Q9ZGI4 and Q9ZGI3 and Q9ZGI2 and Q9ZGI1 Q9ZGI5: type I polyketide synthase PikAI, Q9ZGI4: type I polyketide synthase PikAII, Q9ZGI3: type I polyketide synthase PikAIII, Q9ZGI2: type I polyketide synthase PikAIV, Q9ZGI1: thioesterase II PikAV. Multifunctional, modular enzyme
-

Purification (Commentary)

EC Number Purification (Comment) Organism
2.3.1.240
-
 Streptomyces venezuelae

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.3.1.239 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate + (2S)-methylmalonyl-CoA + NADPH + H+ the engineered polyketide synthase PikAIII-TE(thioesterase domain) fusion protein accepts and processes the pentaketide to produce 10-deoxymethynolide as the sole product. The polyketide synthase PikAIII/polyketide synthase PikAIV complex processes the pentaketide to produce 10-deoxymethynolide and narbonolide. After incubation of the hexaketide with polyketide synthase PikAIII-TE(thioesterase domain) fusion protein in both the presence and absence of NADPH, no product formation is observed Streptomyces venezuelae 10-deoxymethynolide + ?
-
 ?
2.3.1.239 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate + (2S)-methylmalonyl-CoA + NADPH + H+ the engineered polyketide synthase PikAIII-TE(thioesterase domain) fusion protein accepts and processes the pentaketide to produce 10-deoxymethynolide as the sole product. The polyketide synthase PikAIII/polyketide synthase PikAIV complex processes the pentaketide to produce 10-deoxymethynolide and narbonolide. After incubation of the hexaketide with polyketide synthase PikAIII-TE(thioesterase domain) fusion protein in both the presence and absence of NADPH, no product formation is observed Streptomyces venezuelae ATCC 15439 10-deoxymethynolide + ?
-
 ?
2.3.1.240 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate + (2S)-methylmalonyl-CoA + NADPH + H+ the engineered polyketide synthase PikAIII-TE(thioesterase domain) fusion protein accepts and processes the pentaketide to produce 10-deoxymethynolide as the sole product. The polyketide synthase PikAIII/polyketide synthase PikAIV complex processes the pentaketide to produce 10-deoxymethynolide and narbonolide. After incubation of the hexaketide with polyketide synthase PikAIII-TE(thioesterase domain) fusion protein in both the presence and absence of NADPH, no product formation is observed Streptomyces venezuelae narbonolide + ?
-
 ?
2.3.1.240 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate + (2S)-methylmalonyl-CoA + NADPH + H+ the engineered polyketide synthase PikAIII-TE(thioesterase domain) fusion protein accepts and processes the pentaketide to produce 10-deoxymethynolide as the sole product. The polyketide synthase PikAIII/polyketide synthase PikAIV complex processes the pentaketide to produce 10-deoxymethynolide and narbonolide. After incubation of the hexaketide with polyketide synthase PikAIII-TE(thioesterase domain) fusion protein in both the presence and absence of NADPH, no product formation is observed Streptomyces venezuelae ATCC 15439 narbonolide + ?
-
 ?
2.3.1.240 hexaketide N-acetyl cysteamine thioester + (2S)-methylmalonyl-CoA + NADPH + H+ incubation of the monomodular polyketide synthase PikAIV with hexaketide and 2-methylmalonyl-CoA results in chain extension to the final heptaketide, release, and cyclization to afford narbonolide. The polyketide synthase PikAIII/polyketide synthase PikAIV complex processes the pentaketide to produce 10-deoxymethynolide and narbonolide. No activity with (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate (i.e. pentaketide) to produce 10-deoxymethynolide Streptomyces venezuelae narbonolide + ?
-
 ?
2.3.1.240 hexaketide N-acetyl cysteamine thioester + (2S)-methylmalonyl-CoA + NADPH + H+ incubation of the monomodular polyketide synthase PikAIV with hexaketide and 2-methylmalonyl-CoA results in chain extension to the final heptaketide, release, and cyclization to afford narbonolide. The polyketide synthase PikAIII/polyketide synthase PikAIV complex processes the pentaketide to produce 10-deoxymethynolide and narbonolide. No activity with (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate (i.e. pentaketide) to produce 10-deoxymethynolide Streptomyces venezuelae ATCC 15439 narbonolide + ?
-
 ?

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.3.1.239 30
-
 assay at Streptomyces venezuelae
2.3.1.240 30
-
 assay at Streptomyces venezuelae

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
2.3.1.239 0.05
-
 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate pH 7.2, 30°C, kcat for activity with the polyketide synthase PikAIII/polyketide synthase PikAIV complex in formation of 10-deoxymethynolide Streptomyces venezuelae
2.3.1.240 0.055
-
 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate pH 7.2, 30°C, kcat for activity with the polyketide synthase PikAIII/polyketide synthase PikAIV complex in formation of narbonolide Streptomyces venezuelae

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.3.1.239 7.2
-
 assay at Streptomyces venezuelae
2.3.1.240 7.2
-
 assay at Streptomyces venezuelae

kcat/KM [mM/s]

EC Number kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
2.3.1.239 0.2
-
 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate pH 7.2, 30°C, kcat/Km-value for activity with the polyketide synthase PikAIII/polyketide synthase PikAIV complex in formation of 10-deoxymethynolide Streptomyces venezuelae
2.3.1.240 0.13
-
 (E)-(2S,4R,8R,9R)-S-2-acetamidoethyl 9-hydroxy-2,4,8-trimethyl-5-oxoundec-6-enethioate pH 7.2, 30°C, kcat/Km-value for activity with the polyketide synthase PikAIII/polyketide synthase PikAIV complex in formation of narbonolide Streptomyces venezuelae