|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 1.1.1.-
Enzymes and Genes:
|Streptomyces coelicolor A3(2) :||ActVI-ORF1
In Pathway: actinorhodin biosynthesis
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, 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, and some reactions have been computationally balanced for hydrogen by adding free protons. 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): 0.47747803 [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][Taguchi04]. 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].
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
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
Taguchi04: 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-Step Genes for Actinorhodin Biosynthesis." FEMS Microbiol. Lett., Online Early.
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