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Information on EC 3.7.1.17 - 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase for references in articles please use BRENDA:EC3.7.1.17
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EC Tree
IUBMB Comments The enzyme is involved in the bacterial degradation of the steroid ring structure, and is involved in degradation of multiple steroids, such as testosterone , cholesterol , and sitosterol.
The enzyme appears in viruses and cellular organisms
Synonyms
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid hydrolase, HsaD, TesD,
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2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase
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2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid hydrolase
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid hydrolase
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2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid hydrolase
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HsaD
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TesD
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(1E,2Z)-3-hydroxy-5,9,17-trioxo-4,5:9,10-disecoandrosta-1(10),2-dien-4-oate + H2O = 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + (2Z,4Z)-2-hydroxyhexa-2,4-dienoate
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4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase ( (2Z,4Z)-2-hydroxyhexa-2,4-dienoate-forming)
The enzyme is involved in the bacterial degradation of the steroid ring structure, and is involved in degradation of multiple steroids, such as testosterone [1], cholesterol [2], and sitosterol.
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2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
?
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + 2-hydroxy-hexa-2,4-dienoic acid
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best substrate
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-dien-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + 2-hydroxyhexa-2,4-dienoic acid
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + ?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid + H2O
?
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?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
?
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?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
?
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?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
?
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?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
?
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-dien-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + 2-hydroxyhexa-2,4-dienoic acid
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-dien-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + 2-hydroxyhexa-2,4-dienoic acid
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + ?
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the apparent specificity for 4,5–9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid is 34fold higher than for 2-hydroxy-6-oxo-6-phenylpentadienoate
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid + ?
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the apparent specificity for 4,5–9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid is 34fold higher than for 2-hydroxy-6-oxo-6-phenylpentadienoate
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
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high specificity
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
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high specificity
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?
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4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
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high specificity
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?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
?
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high specificity
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?
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3,4-dichloroisocoumarin
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a broad spectrum covalent inhibitor of serine proteases, the structural homologues of 3,4-dichloroisocoumarin, 7-amino-4-chloro-3-methoxy-1H-2-benzopyran and 3-phenyl-1H-2-benzopyran-1-one, show significantly poorer inhibition
3-phenyl-1H-2-benzopyran-1-one
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weak inhibition
4-(2-aminoethyl)benzenesulfonyl fluoride
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weak inhibition
4-amidinophenylmethanesulfonyl fluoride
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weak inhibition
4-nitrophenyl-4-[bis(1,3-benzodioxol-5-yl)(hydroxy)methyl]piperidine-1-carboxylate
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covalent inhibitor
6-carbamimidoylnaphthalen-2-yl 4-carbamimidamidobenzoate
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weak inhibition
7-amino-4-chloro-3-methoxy-1H-2-benzopyran
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weak inhibition
benzamidine
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weak inhibition
eserine
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an acetylcholinesterase inhibitor
leupeptin
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weak inhibition
neostigmine
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an acetylcholinesterase inhibitor
Trichlorfon
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an acetylcholinesterase inhibitor, weak inhibition
additional information
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inhibition of HsaD by serine protease inhibitors. No inhibition by acetylcholinesterase inhibitors edrophonium, tacrine, and pyridostigmine. Consistent with the lack of a cysteine residue in the active site of HsaD, covalent inhibitor nicotinamide does not significantly inhibit HsaD
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0.019
2-hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid
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in 20 mM HEPES, 80 mM NaCl, at pH 8.0 and 25°C
0.008 - 0.23
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.017
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.31
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.008
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.23
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
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apparent value, in 100 mM of phosphate buffer (pH 7.4) with 20 mM NaCl, temperature not specified in the publication
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0.066 - 0.25
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.000085 - 0.55
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
0.33
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.066
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.25
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
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in 100 mM of phosphate buffer (pH 7.4) with 20 mM NaCl, temperature not specified in the publication
0.000085
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
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mutant enzyme S114A, in 100 mM potassium phosphate, pH 7.5, at 25°C
0.55
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
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1.129 - 9
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
33
4,5-9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
1.06
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
1.129
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
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apparent value, in 100 mM of phosphate buffer (pH 7.4) with 20 mM NaCl, temperature not specified in the publication
9
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
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wild type enzyme, in 100 mM potassium phosphate, pH 7.5, at 25°C
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0.63
PMSF
Mycobacterium tuberculosis
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pH 7.5, 21°C, recombinant enzyme
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Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain CDC 1551 / Oshkosh)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
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33800
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x * 33800, His6-tagged enzyme, estimated from SDS-PAGE
132000
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calculated from amino acid sequence
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homotetramer
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x * 33800, His6-tagged enzyme, estimated from SDS-PAGE
homotetramer
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x * 33800, His6-tagged enzyme, estimated from SDS-PAGE
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tetramer
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x-ray crystallography
tetramer
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x-ray crystallography
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mutant enzyme S114A, sitting drop vapor diffusion method, using 200 mM KSCN, 24% polyethylene glycol 3.35 K, and 100 mM bis-tris propane, pH 7.0
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sitting drop vapor diffusion method, using 30% (w/v) PEG 3000, 0.1?M CHES, pH 9.5
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S114A
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the mutant has a 6500fold lower kcat for 4,5–9,10-diseco-3-hydroxy-5,9,17-tri-oxoandrosta-1(10),2-diene-4-oic acid compared to the wild type enzyme
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60 - 70
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the enzyme retains more than 95% of its activity after incubation at 60°C for 30 min. Hydrolytic activity is significantly decreased after incubation at 70°C
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Ni affinity column chromatography
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Ni-NTA column chromatography, gel filtration
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recombinant enzyme from Pseudomonas putida strain KT2442
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Source 15Q anion exchange resin column chromatography
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expressed in Escherichia coli strain GJ1158
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expressed in Pseudomonas putida strain KT2442
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expressed in Pseudomonas putida strain KT4224
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recombinant expression in Pseudomonas putida strain KT2442
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Horinouchi, M.; Hayashi, T.; Yamamoto, T.; Kudo, T.
A new bacterial steroid degradation gene cluster in Comamonas testosteroni TA441 which consists of aromatic-compound degradation genes for seco-steroids and 3-ketosteroid dehydrogenase genes
Appl. Environ. Microbiol.
69
4421-4430
2003
Comamonas testosteroni, Comamonas testosteroni TA441
brenda
Lack, N.; Lowe, E.; Liu, J.; Eltis, L.; Noble, M.; Sim, E.; Westwood, I.
Structure of HsaD, a steroid-degrading hydrolase, from Mycobacterium tuberculosis
Acta Crystallogr. Sect. F
64
2-7
2007
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Lack, N.; Kawamura, A.; Fullam, E.; Laurieri, N.; Beard, S.; Russell, A.; Evangelopoulos, D.; Westwood, I.; Sim, E.
Temperature stability of proteins essential for the intracellular survival of Mycobacterium tuberculosis
Biochem. J.
418
369-378
2009
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Lack, N.; Yam, K.; Lowe, E.; Horsman, G.; Owen, R.; Sim, E.; Eltis, L.
Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism
J. Biol. Chem.
285
434-443
2010
Mycobacterium tuberculosis
brenda
Van Der Geize, R.; Yam, K.; Heuser, T.; Wilbrink, M.; Hara, H.; Anderton, M.; Sim, E.; Dijkhuizen, L.; Davies, J.; Mohn, W.; Eltis, L.
A gene cluster encoding cholesterol catabolism in a soil actinomycete provides insight into Mycobacterium tuberculosis survival in macrophages
Proc. Natl. Acad. Sci. USA
104
1947-1952
2007
Mycobacterium tuberculosis, Mycobacterium tuberculosis H37Rv
brenda
Ryan, A.; Keany, S.; Eleftheriadou, O.; Ballet, R.; Cheng, H.Y.; Sim, E.
Mechanism-based inhibition of HsaD: a C-C bond hydrolase essential for survival of Mycobacterium tuberculosis in macrophage
FEMS Microbiol. Lett.
350
42-47
2014
Mycobacterium tuberculosis
brenda
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3.7.1.17 4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase
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