Information on EC 1.2.1.77 - 3,4-dehydroadipyl-CoA semialdehyde dehydrogenase (NADP+):
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EC NUMBERCOMMENTARY
1.2.1.77-

RECOMMENDED NAMEGeneOntology No.
3,4-dehydroadipyl-CoA semialdehyde dehydrogenase (NADP+)-

REACTIONREACTION DIAGRAMCOMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
3,4-didehydroadipyl-CoA semialdehyde + NADP+ + H2O = 3,4-didehydroadipyl-CoA + NADPH + H+
show the reaction diagram		----
3,4-didehydroadipyl-CoA semialdehyde + NADP+ + H2O = 3,4-didehydroadipyl-CoA + NADPH + H+
show the reaction diagram		-Azoarcus evansii-698572

REACTION TYPEORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

PATHWAYKEGG LinkMetaCyc Link
benzoyl-CoA degradation I (aerobic)-PWY-1361

SYSTEMATIC NAMEIUBMB Comments
3,4-dehydroadipyl-CoA semialdehyde:NADP+ oxidoreductaseThis enzyme catalyses a step in the aerobic benzoyl-coenzyme A catabolic pathway in Azoarcus evansii and Burkholderia xenovorans.

SYNONYMSORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
3,4-dehydroadipyl-CoA semialdehyde dehydrogenaseAzoarcus evansii--698572
ALDHCBurkholderia xenovoransQ13WK4-688414
BoxDAzoarcus evansii--698572, 712441
NADP+-dependent aldehyde dehydrogenaseAzoarcus evansii--712441

CAS REGISTRY NUMBERCOMMENTARY
No entries in this field

ORGANISMCOMMENTARYLITERATURESEQUENCE CODESEQUENCE DB SOURCE
Azoarcus evansii-698572, 712441--Manually annotated by BRENDA team
Azoarcus evansii KB740-712441--Manually annotated by BRENDA team
Burkholderia xenovoransstrain LB400688414Q13WK4UniprotManually annotated by BRENDA team

GENERAL INFORMATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SUBSTRATEPRODUCT                      REACTION DIAGRAMORGANISM UNIPROT ACCESSION NO. COMMENTARY/
Substrate		 LITERATURE/
Substrate		 COMMENTARY/
Product		 LITERATURE/
Product		 Reversibility
r=reversible
ir=irreversible
?=not specified
3,4-dehydroadipyl-CoA semialdehyde + NADP+3,4-dehydroadipyl-CoA + NADPH + H+ + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4the enzyme is involved in the benzoate oxidation (box) pathway688414--?
3,4-dehydroadipyl-CoA semialdehyde + NADP+ + H2O3,4-dehydroadipyl-CoA + NADPH + H+
show the reaction diagram		Azoarcus evansii--712441--?
3,4-dehydroadipyl-CoA semialdehyde + NADP+ + H2O3,4-dehydroadipyl-CoA + NADPH + H+
show the reaction diagram		Azoarcus evansii-enzyme of the aerobic benzoyl-coenzyme A catabolic pathway, the molar ratio of mol of converted substrate per mol of NADPH formed is estimated to be 1698572--?
benzaldehyde + NADP+ + H2Obenzoate + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4-688414--?
formaldehyde + NADP+ + H2Oformate + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4-688414--?
heptaldehyde + NADP+ + H2Oheptanoate + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4-688414--?
propionaldehyde + NADP+ + H2Opropionate + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4-688414--?
valeraldehyde + NADP+ + H2Ovalerate + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4-688414--?
isovaleraldehyde + NADP+ + H2Oisovalerate + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4-688414--?
additional information?-Burkholderia xenovoransQ13WK4the native substrate (3,4-dehydroadipyl-CoA semialdehyde) is not tested as it is commercially unavailable. The enzyme is preferentially active towards linear medium-chain to long-chain aldehydes as compared to branched-chain, short-chain or aromatic aldehydes688414---

NATURAL SUBSTRATESNATURAL PRODUCTSREACTION DIAGRAMORGANISM UNIPROT ACCESSION NO.COMMENTARY SUBSTRATELITERATURE
(Substrate)		COMMENTARY PRODUCTLITERATURE
(Product)
3,4-dehydroadipyl-CoA semialdehyde + NADP+3,4-dehydroadipyl-CoA + NADPH + H+ + NADPH + H+
show the reaction diagram		Burkholderia xenovoransQ13WK4the enzyme is involved in the benzoate oxidation (box) pathway688414--
3,4-dehydroadipyl-CoA semialdehyde + NADP+ + H2O3,4-dehydroadipyl-CoA + NADPH + H+
show the reaction diagram		Azoarcus evansii-enzyme of the aerobic benzoyl-coenzyme A catabolic pathway698572--

COFACTORORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATUREIMAGE
NAD+Burkholderia xenovoransQ13WK4the enzyme is more active in the presence of NADP+ relative to NAD+. Crystallographic data show that cofactor selectivity is governed by a complex network of hydrogen bonds between the oxygen atoms of the 2'-phosphoryl moiety of NADP+ and a threonine/lysine pair on the enzyme688414 2D-image
NADP+Burkholderia xenovoransQ13WK4the enzyme is more active in the presence of NADP+ relative to NAD+. Crystallographic data show that cofactor selectivity is governed by a complex network of hydrogen bonds between the oxygen atoms of the 2'-phosphoryl moiety of NADP+ and a threonine/lysine pair on the enzyme688414 2D-image
NADP+Azoarcus evansii-no activity (below 2%) with NAD+. The molar ratio of mol of converted substrate per mol of NADPH formed is estimated to be 1698572 2D-image
NADP+Azoarcus evansii--712441 2D-image

METALS and IONS ORGANISM UNIPROT ACCESSION NO.COMMENTARY LITERATURE
additional informationAzoarcus evansii-salt concentrations up to 500 mM KCl have no effect on enzyme activity698572

INHIBITORSORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
additional informationAzoarcus evansii-salt concentrations up to 500 mM KCl and EDTA concentrations up to 50 mM have no effect on enzyme activity698572-

ACTIVATING COMPOUNDORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

KM VALUE [mM]KM VALUE [mM] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
0.025-3,4-dehydroadipyl-CoA semialdehydeAzoarcus evansii-pH 7.2698572 2D-image
4.15-benzaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
1.9-formaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.042-heptaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
1.66-IsovaleraldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.501-NAD+Burkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.016-NADP+Azoarcus evansii-pH 7.2698572 2D-image
0.04-NADP+Burkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
1.21-propionaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.3-ValeraldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image

TURNOVER NUMBER [1/s] TURNOVER NUMBER MAXIMUM[1/s] SUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
45-3,4-dehydroadipyl-CoA semialdehydeAzoarcus evansii-pH 7.2698572 2D-image
0.019-benzaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.046-formaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
29.9-heptaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.074-IsovaleraldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
0.501-NAD+Burkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C, cosubstrate: propionaldehyde688414 2D-image
0.04-NADP+Burkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C, cosubstrate: propionaldehyde688414 2D-image
45-NADP+Azoarcus evansii-pH 7.2698572 2D-image
2.32-propionaldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image
5.16-ValeraldehydeBurkholderia xenovoransQ13WK4in 50 mM Tris-HCl (pH 7.5), at 25°C688414 2D-image

kcat/KM VALUE [1/mMs-1]kcat/KM VALUE [1/mMs-1] MaximumSUBSTRATEORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

Ki VALUE [mM]Ki VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

IC50 VALUE [mM]IC50 VALUE [mM] MaximumINHIBITORORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE IMAGE
No entries in this field

SPECIFIC ACTIVITY [µmol/min/mg] SPECIFIC ACTIVITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
0.17-Azoarcus evansii-extracts of cells grown aerobically on benzoate698572

pH OPTIMUMpH MAXIMUMORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
7.2-Azoarcus evansii--698572

pH RANGEpH RANGE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
6.28.8Azoarcus evansii-50% of maximal activity at pH 6.2 and pH 8.8698572

TEMPERATURE OPTIMUMTEMPERATURE OPTIMUM MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

TEMPERATURE RANGE TEMPERATURE MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

pI VALUEpI VALUE MAXIMUMORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

SOURCE TISSUE ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE SOURCE
No entries in this field

LOCALIZATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY GeneOntology No. LITERATURE SOURCE
No entries in this field

PDBSCOPCATHORGANISM
No entries in this field

MOLECULAR WEIGHT MOLECULAR WEIGHT MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

SUBUNITS ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
?Burkholderia xenovoransQ13WK4forms a dimer in solution with a molecular mass of 110000, SDS-PAGE688414
dimerAzoarcus evansii-2 * 54000698572
homodimerAzoarcus evansii-2 * 54000712441

POSTTRANSLATIONAL MODIFICATION ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

Crystallization/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
sitting drop vapour diffusion method, at 18°C in 29% PEG 3350K and 100 mM bis-Tris (pH 6.0), 1.6 A crystal structure of ALDHC in complex with NADPH bound in the cofactor-binding pocket and an ordered fragment of a polyethylene glycol molecule bound in the substrate tunnelBurkholderia xenovoransQ13WK4688414

pH STABILITYpH STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

TEMPERATURE STABILITYTEMPERATURE STABILITY MAXIMUM ORGANISM UNIPROT ACCESSION NO. COMMENTARYLITERATURE
No entries in this field

GENERAL STABILITYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

ORGANIC SOLVENT ORGANISM UNIPROT ACCESSION NO. COMMENTARY LITERATURE
No entries in this field

OXIDATION STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

STORAGE STABILITY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-20°C, enzyme could be stored without appreciable loss of activity for months at -20°C in the presence of 10% (v/v) glycerolAzoarcus evansii-698572

Purification/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
-Azoarcus evansii-698572, 712441
-Burkholderia xenovoransQ13WK4688414

Cloned/COMMENTARY ORGANISM UNIPROT ACCESSION NO. LITERATURE
expression in Escherichia coli as a protein tagged at its N terminus with maltose-binding proteinAzoarcus evansii-698572
expressed in Escherichia coli BL21 Star (DE3) cellsBurkholderia xenovoransQ13WK4688414

EXPRESSION ORGANISM UNIPROT ACCESSION NO. LITERATURE
No entries in this field

ENGINEERINGORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

Renatured/COMMENTARYORGANISM UNIPROT ACCESSION NO.LITERATURE
No entries in this field

APPLICATIONORGANISM UNIPROT ACCESSION NO.COMMENTARYLITERATURE
No entries in this field

REF. AUTHORS TITLE JOURNAL VOL. PAGES YEAR ORGANISMLINK TO PUBMEDSOURCE
688414Bajns J., Boulanger MJ.Structural and biochemical characterization of a novel aldehyde dehydrogenase encoded by the benzoate oxidation pathway in Burkholderia xenovorans LB400J. Mol. Biol.379597-6082008Burkholderia xenovorans PubMed
698572Gescher, J.; Ismail, W.; Olgeschläger, E.; Eisenreich, W.; Wörth, J.; Fuchs, G.Aerobic benzoyl-coenzyme A (CoA) catabolic pathway in: conversion of ring cleavage product by 3,4-dehydroadipyl-CoA semialdehyde dehydrogenaseJ. Bacteriol.1882919-29272006Azoarcus evansii PubMed
712441Rather, L.J.; Knapp, B.; Haehnel, W.; Fuchs, G.Coenzyme A-dependent aerobic metabolism of benzoate via epoxide formationJ. Biol. Chem.28520615-206242010Azoarcus evansii PubMed

LINKS TO OTHER DATABASES (specific for EC-Number 1.2.1.77)
ExplorEnz
ExPASy
KEGG
MetaCyc
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)