MetaCyc Reaction: 1.1.1.-

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number: 1.1.1.-

Enzymes and Genes:

Streptomyces coelicolor A3(2): ActVI-ORF1Inferred from experiment: SCO5072

In Pathway: actinorhodin biosynthesis

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the direction in which it was curated.

Most BioCyc compounds have been protonated to a reference pH value of 7.3. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Enzyme Commission Primary Name: 1.1.1 -- With NAD(+) or NADP(+) as acceptor

Standard Gibbs Free Energy (ΔrG in kcal/mol): 0.47747803Inferred by computational analysis [Latendresse13]

ActVI-ORF1 catalyzes the reduction of 4-(3'-acetyl-5'-hydroxy-4'-oxo-1',4'-dihydronapthalen-2'-yl)-3-oxobutanoate at C-3 via two active amino acids, Glu141 and His129, and NAD(P)H to yield a secondary alcohol [FernandezMoreno94][Ichinose99][Taguchi00][Taguchi04a]. It was also discovered that the likely substrate for ActVI-ORF1 is the β-keto acid form of the bicyclic intermediate, thus indicating that the ACP is released prior to this reaction [BookerMilburn05].

Citations: [Taguchi07, Tahlan07, Kanehisa05]

Gene-Reaction Schematic

Gene-Reaction Schematic


BookerMilburn05: Booker-Milburn KI, Gillan R, Kimberley M, Taguchi T, Ichinose K, Stephenson GR, Ebizuka Y, Hopwood DA (2005). "Enantioselective reduction of beta-keto acids with engineered Streptomyces coelicolor." Angew Chem Int Ed Engl 44(7);1121-5. PMID: 15645472

FernandezMoreno94: Fernandez-Moreno MA, Martinez E, Caballero JL, Ichinose K, Hopwood DA, Malpartida F (1994). "DNA sequence and functions of the actVI region of the actinorhodin biosynthetic gene cluster of Streptomyces coelicolor A3(2)." J Biol Chem 269(40);24854-63. PMID: 7929165

Ichinose99: Ichinose K, Surti C, Taguchi T, Malpartida F, Booker-Milburn KI, Stephenson GR, Ebizuka Y, Hopwood DA (1999). "Proof that the ACTVI genetic region of Streptomyces coelicolor A3(2) is involved in stereospecific pyran ring formation in the biosynthesis of actinorhodin." Bioorg Med Chem Lett 9(3);395-400. PMID: 10091691

Kanehisa05: Kanehisa Laboratories (2005). "Biosynthesis of Type II Polyketide Products." KEGG: Kyoto Encyclopedia of Genes and Genomes. PMID: 16381885

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Taguchi00: Taguchi T, Itou K, Ebizuka Y, Malpartida F, Hopwood DA, Surti CM, Booker-Milburn KI, Stephenson GR, Ichinose K (2000). "Chemical characterisation of disruptants of the Streptomyces coelicolor A3(2) actVI genes involved in actinorhodin biosynthesis." J Antibiot (Tokyo) 53(2);144-52. PMID: 10805574

Taguchi04a: Taguchi T, Kunieda K, Takeda-Shitaka M, Takaya D, Kawano N, Kimberley MR, Booker-Milburn KI, Stephenson GR, Umeyama H, Ebizuka Y, Ichinose K (2004). "Remarkably different structures and reaction mechanisms of ketoreductases for the opposite stereochemical control in the biosynthesis of BIQ antibiotics." Bioorg Med Chem 12(22);5917-27. PMID: 15498668

Taguchi07: Taguchi, T., et al. (2007). "Possible Involvement of ActVI-ORFA in Transcriptional Regulation of actVI Tailoring-StepGenes for Actinorhodin Biosynthesis." FEMS Microbiol. Lett., Online Early.

Tahlan07: Tahlan, K., et al (2007). "Initiation of Actinorhodin export in Streptomyces coelicolor." Molecular Microbiology, OnlineEarly Articles.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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