Information on EC 2.3.1.236 - 5-methylnaphthoic acid synthase

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The expected taxonomic range for this enzyme is: Streptomyces sahachiroi

EC NUMBER
COMMENTARY hide
2.3.1.236
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RECOMMENDED NAME
GeneOntology No.
5-methylnaphthoic acid synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
acetyl-CoA + 5 malonyl-CoA + 3 NADPH + 3 H+ = 5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 4 H2O + 3 NADP+
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:acetyl-CoA malonyltransferase (5-methyl-1-naphthoic acid forming)
A multi-domain polyketide synthase involved in the synthesis of azinomycin B in the bacterium Streptomyces griseofuscus.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
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the multi-domain polyketide synthase involved in the synthesis of azinomycin B
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + 5 malonyl-CoA + 3 NADPH + 3 H+
5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 4 H2O + 3 NADP+
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + 5 malonyl-CoA + 3 NADPH + 3 H+
5-methyl-1-naphthoate + 6 CoA + 5 CO2 + 4 H2O + 3 NADP+
show the reaction diagram
B4XYB8
the multi-domain polyketide synthase involved in the synthesis of azinomycin B
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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heterologous expression of aziB in Streptomyces albus. Addition of aziB1 (encoding a P450 hydroxylase) and aziB2 (encoding an O-methyltransferase) to aziB in Streptomyces albus allows for the production of 3-methoxy-5-methyl-naohthoic acid as the first building block for skeleton assembly of azinomycin B
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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constructs harboring mutant aziB, in which site specific mutations are performed for inactivating the KR and DH domains, respectively, are introduced into Streptomyces albus, yielding the recombinant strain AL1007 (to express the KR mutant AziB, G1398A within the NADPH-binding motif GxGxxG), AL1008 (to express the KR mutant AziB, Y1549F at the conserved active site), and AL1009 (to express the DH mutant AziB, H935F within the conserved motif HxxxGxxxxP). Upon HPLC-MS analysis, AL1007, AL1008, and AL1009 fail to produce 5-methyl-NPA, confirming that the reductive and dehydrating actions governed by the KR and DH domains of AziB are essential for the 5-methyl-naphthoic acid formation