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Information on EC 4.5.1.B1 - hexachlorocyclohexane dehydrochlorinase
for references in articles please use BRENDA:EC4.5.1.B1preliminary BRENDA-supplied EC number
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EC Tree
4.5.1.B1 hexachlorocyclohexane dehydrochlorinaseSpecify your search results
Word Map
- 4.5.1.B1
-
dehydrochlorination
- paucimobilis
-
enantiomer
- sphingobium
- indicum
- lindane
-
enantioselectivity
-
insecticide
-
pesticide
- 1,2,4-trichlorobenzene
-
hexabromocyclododecanes
-
hbcds
-
archetypal
-
stockholm
-
dehalogenase
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
lina2, lina1, lina-type2, lina-type1, gamma-hch dehydrochlorinase, lina-ut26, hexachlorocyclohexane dehydrochlorinase, hch dehydrochlorinase, gamma-hexachlorocyclohexane dehydrochlorinase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
gamma-HCH dehydrochlorinase
gamma-hexachlorocyclohexane dehydrochlorinase
HCH dehydrochlorinase
LinA
Lina1
Lina2
HCH dehydrochlorinase
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
1,3,4,5,6-pentachlorocyclohexene = 1,3,4,6-tetrachlorocyclohexa-1,4-diene + HCl
-
-
-
-
hexachlorocyclohexane = 1,3,4,5,6-pentachlorocyclohexene + HCl
-
-
-
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(1R,2R,3S,4S,5S,6S)-1,2,3,4,5,6-hexachlorocyclohexane
1,3,4,5,6-pentachlorocyclohex-1-ene + HCl
(1R,2R,3R,4R,5S,6S)-hexachlorocyclohexane
1,3,4,5,6-pentachlorocyclohex-1-ene + HCl
i.e. (+)-alpha-hexachlorocyclohexane. Isoform LinA1 shows enantioselectivity for the substrate and the product formed
-
-
?
(1R,2R,3R,4R,5S,6S)-hexachlorocyclohexane
1,3,4,5,6-pentachlorocyclohex-1-ene + HCl
i.e. (+)-alpha-hexachlorocyclohexane. Isoform LinA1 shows enantioselectivity for the substrate and the product formed
-
-
?
(1R,2R,3S,4S,5S,6S)-1,2,3,4,5,6-hexachlorocyclohexane
1,3,4,5,6-pentachlorocyclohex-1-ene + HCl
i.e. (-)-alpha-hexachlorocyclohexane. Isoform LinA2 shows enantioselectivity for the substrate and the product formed
-
-
?
(1R,2R,3S,4S,5S,6S)-1,2,3,4,5,6-hexachlorocyclohexane
1,3,4,5,6-pentachlorocyclohex-1-ene + HCl
i.e. (-)-alpha-hexachlorocyclohexane. Isoform LinA2 shows enantioselectivity for the substrate and the product formed
-
-
?
1,3,4,5,6-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
1,3,4,5,6-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
1,3,4,5,6-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
alpha-hexachlorocyclohexane
beta-pentachlorocyclohexene + HCl
-
the product spontaneously reacts to 1,2,4-trichlorobenzene + HCl
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
delta-pentachlorocyclohexene is formed as an intermediate
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
delta-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
-
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
Sphingobium indicum DSM 16413
-
-
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
1,3,4,6-tetrachloro-1,4-cyclohexadiene + 2 HCl
-
gamma-pentachlorocyclohexene is formed as an intermediate
-
?
gamma-hexachlorocyclohexane
gamma-pentachlorocyclohexene + HCl
-
-
-
-
?
gamma-hexachlorocyclohexane
gamma-pentachlorocyclohexene + HCl
-
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
activity differs with isomers alpha, gamma, and delta, for LinA type 1 the activity is highest with the alpha isomer, no activity with the beta isomer
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
-
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
activity differs with isomers alpha, gamma, and delta, for LinA type 1 the activity is highest with the gamma-isomer, no activity with the beta isomer
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
activity differs with isomers alpha, gamma, and delta, for LinA type 2 the activity is highest with the alpha-isomer, no activity with the beta isomer
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
activity differs with isomers alpha, gamma, and delta, LinA-type1 exhibits enantioselectivity for the (-)-enantiomer of alpha-hexachlorocyclohexane
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
activity differs with isomers alpha, gamma, and delta, LinA-type2 exhibits enantioselectivity for the (+)-enantiomer of alpha-hexachlorocyclohexane
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
1,3,4,5,6-pentachlorocyclohexene
1,3,4,6-tetrachloro-1,4-cyclohexadiene + HCl
-
-
-
?
gamma-hexachlorocyclohexane
pentachlorocyclohexene + HCl
-
-
-
?
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
20 - 65
activity range, rapid drop in activity above 60°C, profile overview
30 - 75
activity range, rapid drop in activity above 70°C, profile overview
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
brenda
LinA-type 1, sequence of LinA-type1, B5ANV6, is 100% identical to LinA-UT26; i.e. Pseudomonas paucimobilis, gene linA-UT26
UniProt
brenda
LinA-type 1, sequence of LinA-type1 is 100% identical to LinA-UT26, P51697; isolated from soil, gene linA
UniProt
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
changed residues K20Q, L96C and A131G, vicinal to the active site, are probably responsible for the altered enantioselectivity of LinA-type2 compared to LinA-type1, structural comparison of LinA-type2 and -type1 proteins suggests that thermostability of LinA-type2 might partly arise due to presence of higher number of ionic interactions, along with 4% increase in the intersubunit buried surface area
metabolism
additional information
metabolism
the enzyme mediates the first step of aerobic degradation of a chlorinated insecticide gamma-hexachlorocyclohexane
metabolism
the enzyme mediates the first step of aerobic degradation of a chlorinated insecticide gamma-hexachlorocyclohexane
metabolism
the enzyme mediates the first step of aerobic degradation of a chlorinated insecticide gamma-hexachlorocyclohexane
additional information
active site structure, structure comparison and docking modeling, overview
additional information
active site structure, structure comparison and docking modeling, overview
additional information
LinA-type2 differs from archetypal LinA-UT26 by ten residues i.e. K20Q, A23G, F68Y, C71T, L96C, F113Y, D115 N, R129L, A131G and T133 M
additional information
LinA-type2 differs from archetypal LinA-UT26 by ten residues i.e., K20Q, A23G, F68Y, C71T, L96C, F113Y, D115 N, R129L, A131G and T133 M
additional information
LinA-type2 differs from archetypal LinA-UT26 by ten residues i.e., K20Q, A23G, F68Y, C71T, L96C, F113Y, D115 N, R129L, A131G and T133 M
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). LINA_SPHJU
Sphingobium japonicum (strain DSM 16413 / CCM 7287 / MTCC 6362 / UT26 / NBRC 101211 / UT26S)
156
0
17342
Swiss-Prot
-
LINA1_SPHIB
Sphingobium indicum (strain DSM 16412 / CCM 7286 / MTCC 6364 / B90A)
154
0
17145
Swiss-Prot
Chloroplast (Reliability: 4)
LINA2_SPHIB
Sphingobium indicum (strain DSM 16412 / CCM 7286 / MTCC 6364 / B90A)
156
0
17342
Swiss-Prot
-
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
16500
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
homotetramer
homotrimer
homotetramer
4 * 16500
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
quantum mechanics/molecular mechanics study. In the degradation process, two discontinuous dehydrochlorination reactions with the Boltzmann-weighted average potential barriers of 16.2 and 17.3 kcal/mol are connected by a conformational transition with a barrier of 11.1 kcal /mol. Residue Phe68 facilitates the dehydrochlorination of gamma-hexachlorohexane, whereas Leu21 and Cys71 suppress it
using 100 mM HEPES-Na (pH 7.0), 16% (w/v) polyethylene glycol 3350, and 200 mM ammonium acetate
-
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
45
70
additional information
additional information
residues Q20 and G23 are determinants of thermostability for LinA-type2
additional information
residues Q20 and G23 are determinants of thermostability for LinA-type2
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene linA, DNA and amino acid sequence and genetic structure analysis
gene linA, DNA and amino acid sequence determination and analysis, genetic structure analysis
gene linA, DNA and amino acid sequence determination and analysis, sequence comparison, subcloning in Escherichia coli strain DH5alpha, expression of C-terminally His-tagged enzyme in Escherichia coli strain BL21(DE3)
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zhang, H.; Wan, H.; Song, L.; Jiang, H.; Wang, H.; Qiao, C.
Development of an autofluorescent Pseudomonas nitroreducens with dehydrochlorinase activity for efficient mineralization of gamma-hexachlorocyclohexane (gamma-HCH)
J. Biotechnol.
146
114-119
2010
Sphingomonas paucimobilis (P51697)
brenda
Okai, M.; Kubota, K.; Fukuda, M.; Nagata, Y.; Nagata, K.; Tanokura, M.
Crystal structure of gamma-hexachlorocyclohexane dehydrochlorinase LinA from Sphingobium japonicum UT26
J. Mol. Biol.
403
260-269
2010
Sphingobium indicum, Sphingobium indicum UT26
brenda
Lal, R.; Pandey, G.; Sharma, P.; Kumari, K.; Malhotra, S.; Pandey, R.; Raina, V.; Kohler, H.P.; Holliger, C.; Jackson, C.; Oakeshott, J.G.
Biochemistry of microbial degradation of hexachlorocyclohexane and prospects for bioremediation
Microbiol. Mol. Biol. Rev.
74
58-80
2010
Sphingomonas paucimobilis (P51697), Sphingomonas paucimobilis (Q5EDH7), Sphingomonas sp. (Q599S6), Sphingomonas sp. (Q599S7), Sphingomonas sp. (Q599S8), Sphingomonas sp. (Q599S9), Sphingomonas sp. (Q599T0), Sphingomonas sp. (Q599T1), Sphingomonas sp. (Q599T2), Sphingomonas sp. (Q599T3), Sphingomonas sp. DS2 (Q599T2), Sphingomonas sp. DS2 (Q599T3), Sphingomonas sp. alpha4-2 (Q599S7), Sphingomonas sp. gamma12-7 (Q599T0), Sphingomonas sp. gamma1-7 (Q599T1), Sphingomonas sp. gamma16-1 (Q599S9), Sphingomonas sp. alpha1-2 (Q599S8), Sphingomonas sp. DS3-1 (Q599S6)
brenda
Macwan, A.S.; Javed, S.; Kumar, A.
Isolation of a novel thermostable dehydrochlorinase (LinA) from a soil metagenome
3 Biotech
1
193-198
2011
uncultured bacterium (B5ANU3), uncultured bacterium (B5ANV6), Sphingomonas paucimobilis (P51697)
brenda
Ito, M.; Ono, A.; Ohtsubo, Y.; Tsuda, M.; Nagata, Y.
Cloning of gamma-hexachlorocyclohexane dehydrochlorinase gene with its flanking regions from soil by activity-based screening techniques
Eur. J. Soil Biol.
52
16-19
2012
Sphingobium indicum (D4Z258), Sphingobium indicum (P59767), Sphingobium indicum (Q6VQZ2), Sphingomonas paucimobilis (Q5EDH7), Sphingobium indicum B90 (P59767), Sphingobium indicum B90A (Q6VQZ2), Sphingobium indicum UT26 (D4Z258)
-
brenda
Macwan, A.S.; Kukshal, V.; Srivastava, N.; Javed, S.; Kumar, A.; Ramachandran, R.
Crystal structure of the hexachlorocyclohexane dehydrochlorinase (LinA-type2): mutational analysis, thermostability and enantioselectivity
PLoS ONE
7
e50373
2012
uncultured bacterium (B5ANU3), uncultured bacterium (B5ANV6)
brenda
Suar, M.; Hauser, A.; Poiger, T.; Buser, H.R.; Mller, M.D.; Dogra, C.; Raina, V.; Holliger, C.; van der Meer, J.R.; Lal, R.; Kohler, H.P.
Enantioselective transformation of a-hexachlorocyclohexaneby the dehydrochlorinases LinA1 and LinA2 from the soil bacterium Sphingomonas paucimobilis B90A
Appl. Environ. Microbiol.
71
8514-8518
2005
Sphingobium indicum (P59766), Sphingobium indicum (P59767), Sphingobium indicum B90A (P59766), Sphingobium indicum B90A (P59767)
brenda
Tang, X.; Zhang, R.; Zhang, Q.; Wang, W.
Dehydrochlorination mechanism of gamma-hexachlorocyclohexane degraded by dehydrochlorinase LinA from Sphingomonas paucimobilis UT26
RSC Adv.
6
4183-4192
2016
Sphingobium indicum (P51697), Sphingobium indicum DSM 16413 (P51697)
-
brenda
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Release 2023.1 (January 2023)
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