Information on EC 6.3.2.47 - dapdiamide synthase

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The expected taxonomic range for this enzyme is: Pantoea agglomerans

EC NUMBER
COMMENTARY hide
6.3.2.47
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RECOMMENDED NAME
GeneOntology No.
dapdiamide synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ATP + 3-({[(2R,3R)-3-carbamoyloxiran-2-yl]carbonyl}amino)-L-alanine + L-valine = ADP + phosphate + 3-({[(2R,3R)-3-carbamoyloxiran-2-yl]carbonyl}amino)-L-alanyl-L-valine
show the reaction diagram
(4)
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ATP + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine + L-isoleucine = ADP + phosphate + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-isoleucine
show the reaction diagram
(2)
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ATP + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine + L-leucine = ADP + phosphate + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-leucine
show the reaction diagram
(3)
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ATP + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine + L-valine = ADP + phosphate + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-valine
show the reaction diagram
(1)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
dapdiamides biosynthesis
SYSTEMATIC NAME
IUBMB Comments
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine:L-valine ligase (ADP-forming)
The enzyme, characterized from the bacterium Pantoea agglomerans, is involved in biosynthesis of dapdiamide tripeptide antibiotics, a family of fumaramoyl- and epoxysuccinamoyl-peptides named for the presence of an (S)-2,3-diaminopropanoate (DAP) moiety and two amide linkages in their scaffold.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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gene DdaF belongs to the dapdiamide antibiotic biosynthetic gene cluster. DdaF acts as a second ATP-dependent amide ligase, cleaving ATP to ADP and Pi during amide bond formation. DdaF adds Val, Ile, or Leu to the carboxylate of fumaramoyl-2,3-diaminopropionate to make the three dapdiamides A-C. To build the dapdiamide antibiotic scaffold, amidation must occur on the fumaroyl-diaminopropionate scaffold, after DdaG action but before DdaF catalysis
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
ATP + 3-((((2R,3R)-3-carboxyoxiran-2-yl)carbonyl)amino)-L-alanine + L-valine
ADP + phosphate + 3-((((2R,3R)-3-carboxyoxiran-2-yl)carbonyl)amino)-L-alanyl-L-valine
show the reaction diagram
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i.e. N-beta-epoxysuccinamoyl-2,3-diaminopropionate. DdaF can catalyze the ligation of both Nbeta-trans-epoxysuccinamoyl-diaminopropionate diastereomers to Val to produce the Nbeta-trans-epoxysuccinamoyl-diaminopropionate-L-valine dipeptide antibiotics. DdaF uses (R,R)-Nbeta-trans-epoxysuccinamoyl-diaminopropionate as a saturable substrate, whereas saturation is not achieved with (S,S)-Nbeta-trans-epoxysuccinamoyl-diaminopropionate at concentrations up to 590 microM
product is a natural antibiotic
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?
ATP + 3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine + L-isoleucine
ADP + phosphate + 3-(((2E)-4-amino-4-oxobut-2-enoyl)amino)-L-alanyl-L-isoleucine
show the reaction diagram
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?
ATP + 3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine + L-leucine
ADP + phosphate + 3-(((2E)-4-amino-4-oxobut-2-enoyl)amino)-L-alanyl-L-leucine
show the reaction diagram
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?
ATP + 3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine + L-valine
ADP + phosphate + 3-(((2E)-4-amino-4-oxobut-2-enoyl)amino)-L-alanyl-L-valine
show the reaction diagram
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?
ATP + 3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine + L-valine
ADP + phosphate + 3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanyl-L-valine
show the reaction diagram
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i.e. Nbeta-fumaramoyl-diaminopropionate
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additional information
?
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DdaF will not accept Nbeta-fumaroyl-diaminopropionate or Nalpha-fumaramoyl-diaminopropionate. The enzyme requires the fumaroyl moiety to be first converted to the fumaramoyl half amide in Nbeta-fumaramoyl-diaminopropionate
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Nbeta-fumaramoyl-diaminopropionate
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substrate inhibition above 0.5 mM
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.053
3-((((2R,3R)-3-carboxyoxiran-2-yl)carbonyl)amino)-L-alanine
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pH 8.0, 22C
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0.072
3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine
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pH 8.0, 22C
0.83
L-isoleucine
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pH 8.0, 22C
7.82
L-leucine
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pH 8.0, 22C
0.26
L-valine
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pH 8.0, 22C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3
3-((((2R,3R)-3-carboxyoxiran-2-yl)carbonyl)amino)-L-alanine
Pantoea agglomerans
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pH 8.0, 22C
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0.3
3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine
Pantoea agglomerans
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pH 8.0, 22C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
56.7
3-((((2R,3R)-3-carboxyoxiran-2-yl)carbonyl)amino)-L-alanine
Pantoea agglomerans
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pH 8.0, 22C
210621
4.83
3-[[(2E)-4-amino-4-oxobut-2-enoyl]amino]-L-alanine
Pantoea agglomerans
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pH 8.0, 22C
209017
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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