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Information on EC 1.13.11.87 - endo-cleaving rubber dioxygenase
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1.13.11.87 endo-cleaving rubber dioxygenaseIUBMB Comments
The enzyme catalyses the cleavage of the double bonds in natural and synthetic rubber, producing a mixture of C20, C25, C30, and higher oligo-isoprenoids with ketone and aldehyde groups at their ends. Two unrelated bacterial enzymes are known to possess this activity - the enzyme from Streptomyces sp. K30 (Lcp) contains a b-type cytochrome, while the enzyme from Xanthomonas sp. 35Y, (RoxB) contains two c-type cytochromes. Both enzymes attack the substrate at random locations, and are not able to cleave the C35 or smaller products into shorter fragments.
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Word Map
- 1.13.11.87
-
polycis-1,4-isoprene
-
rubber-degrading
-
roxas
- xanthomonas
- waste
- gordonia
- polyisoprenivorans
- oxygenases
- heme
-
c-type
-
muteins
- nocardia
-
dihaem
- lividans
-
abrasion
-
tires
- synthesis
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Cleavage of cis-1,4-polyisoprene polymers into a mixture of compounds, including a C20 compound ((4Z,8Z,12Z,16Z,20Z,24Z)-4,8,12,16,20,24-hexamethyl-28-oxononacosa-4,8,12,16,20,24-hexaenal), a C25 compound ((4Z,8Z,12Z,16Z,20Z)-4,8,12,16,20-pentamethyl-24-oxopentacosa-4,8,12,16,20-pentaenal), a C30 compound ((4Z,8Z,12Z,16Z)-4,8,12,16-tetramethyl-20-oxohenicosa-4,8,12,16-tetraenal), and larger isoprenologes such as C35, C40, C45, and higher analogues
Synonyms
lcp1vh2, latex clearing protein, lcpk30, latex-clearing protein, lcp protein, lcp2vh2, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
GPOL_174p00150
GPOL_c48310
latex clearing protein
latex-clearing protein
Lcp
Lcp protein
Lcp1
lcp1VH2
Lcp2
polyisoprene-cleaving rubber oxygenase
RoxB
rubber oxidizing protein
rubber oxygenase
rubber oxygenase B
latex clearing protein
-
-
-
-
Lcp
-
-
-
-
RoxB
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cleavage of cis-1,4-polyisoprene polymers into a mixture of compounds, including a C20 compound ((4Z,8Z,12Z,16Z,20Z,24Z)-4,8,12,16,20,24-hexamethyl-28-oxononacosa-4,8,12,16,20,24-hexaenal), a C25 compound ((4Z,8Z,12Z,16Z,20Z)-4,8,12,16,20-pentamethyl-24-oxopentacosa-4,8,12,16,20-pentaenal), a C30 compound ((4Z,8Z,12Z,16Z)-4,8,12,16-tetramethyl-20-oxohenicosa-4,8,12,16-tetraenal), and larger isoprenologes such as C35, C40, C45, and higher analogues
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-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
cis-1,4-polyisoprene:oxygen dioxygenase (endo-cleaving)
The enzyme catalyses the cleavage of the double bonds in natural and synthetic rubber, producing a mixture of C20, C25, C30, and higher oligo-isoprenoids with ketone and aldehyde groups at their ends. Two unrelated bacterial enzymes are known to possess this activity - the enzyme from Streptomyces sp. K30 (Lcp) contains a b-type cytochrome, while the enzyme from Xanthomonas sp. 35Y, (RoxB) contains two c-type cytochromes. Both enzymes attack the substrate at random locations, and are not able to cleave the C35 or smaller products into shorter fragments.
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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
poly(cis-1,4-isoprene) + O2
(4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
12-oxo-4,8-dimethyltrideca-4,8-diene-1-al is the main cleavage product in the absence of (18)O-compounds. Incorporation of one (18)O atom in 12-oxo-4,8-dimethyltrideca-4,8-diene-1-al is found if the cleavage reaction is performed in the presence of (18)O2 and H2(16)O. Incubation of poly(cis-1,4-isoprene) (with RoxA) or of isolated unlabeled 12-oxo-4,8-dimethyltrideca-4,8-diene-1-al (without RoxA) with H2(18)O in the presence of (16)O2 indicates that the carbonyl oxygen atoms of 12-oxo-4,8-dimethyltrideca-4,8-diene-1-al is significantly exchanged with oxygen atoms derived from water. The isotope exchange is avoided by simultaneous enzymatic reduction of both carbonyl functions of 12-Oxo-4,8-dimethyltrideca-4,8-diene-1-al to the corresponding dialcohol 12-hydroxy-4,8-dimethyltrideca-4,8-diene-1-ol during RoxA-mediated in vitro cleavage of poly(cis-1,4-isoprene)
-
-
?
poly(cis-1,4-isoprene) + O2
(4Z,8Z,12Z,16Z,20Z,24Z)-4,8,12,16,20,24-hexamethyl-28-oxononacosa-4,8,12,16,20,24-hexaenal + (4Z,8Z,12Z,16Z,20Z)-4,8,12,16,20-pentamethyl-24-oxopentacosa-4,8,12,16,20-pentaenal + (4Z,8Z,12Z,16Z)-4,8,12,16-tetramethyl-20-oxohenicosa-4,8,12,16-tetraenal + ?
the enzyme cleaves cis-1,4-polyisoprene polymers into a mixture of C20, C25, and higher oligo-isoprenoids with terminal aldehyde and keto groups were identified
-
-
?
rubber latex + O2
(4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
RoxA cleaves rubber by a dioxygenase mechanism
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-
?
carbon black filled vulcanized rubber + O2
oligo(cis-1,4-isoprenoids)
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-
-
-
?
carbon black filled vulcanized rubber + O2
oligo(cis-1,4-isoprenoids)
-
-
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
Nocardia farcinica NVL3
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
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-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme produces cis-oligo-isoprenoid molecules with a range of n = 4 (299 g/mol) to n = 37 (1423 g/mol) where n is equal to the number of isoprene units of the oligo-isoprenoid molecules
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme produces cis-oligo-isoprenoid molecules with a range of n = 4 (299 g/mol) to n = 37 (1423 g/mol) where n is equal to the number of isoprene units of the oligo-isoprenoid molecules
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-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
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-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves cis-1,4-polyisoprene to a mixture of C20 and higher oligoisoprenoids
-
-
?
cis-1,4-polyisoprene + n O2
?
Solimonas fluminis HR-BB
-
the enzyme cleaves cis-1,4-polyisoprene to a mixture of C20 and higher oligoisoprenoids
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
n (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
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-
-
?
cis-1,4-polyisoprene + n O2
n (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
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-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is essential for the microbial utilization of rubber
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is essential for the microbial utilization of rubber
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-
?
cis-1,4-polyisoprene + O2
?
the enzyme is involved in rubber degradation
-
-
?
cis-1,4-polyisoprene + O2
?
-
the enzyme is involved in rubber degradation
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-
?
cis-1,4-polyisoprene + O2
?
Nocardia farcinica DSM 43665T
the enzyme is involved in rubber degradation
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-
?
cis-1,4-polyisoprene + O2
?
the enzyme is involved in rubber degradation
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-
?
cis-1,4-polyisoprene + O2
?
-
Gram-negative rubber-degrading bacteria generally utilise two synergistically acting rubber oxygenases (RoxA/RoxB) for efficient cleavage of polyisoprene to (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
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-
?
cis-1,4-polyisoprene + O2
?
-
Gram-negative rubber-degrading bacteria generally utilise two synergistically acting rubber oxygenases (RoxA/RoxB) for efficient cleavage of polyisoprene to (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is involved in the initial cleavage of poly(cis-1,4-isoprene)
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-
?
cis-1,4-polyisoprene + O2
?
Lcp degrades polyisoprene via endo-type cleavage to tetra-C20 and higher oligo-isoprenoids with aldehyde and keto end groups
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-
?
cis-1,4-polyisoprene + O2
?
the enzyme acts as an endo-type dioxygenase producing C20 and higher oligo-isoprenoids that differ in the number of isoprene units but have the same terminal functions, CHO-CH2- and -CH2-COCH3
-
-
?
cis-1,4-polyisoprene + O2
?
the three DUF2236 domain-specific residues (R164, T168, and H198) and two conserved arginines (R195 and R202) are essential for activity, stability, and/or incorporation of the heme cofactor in the enzyme
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-
?
cis-1,4-polyisoprene rubber particles + O2
?
the mass distribution of the degradation products differs depending on the extraction solvent. In the presence of pentane, at least 21 oligo(cis-1,4-isoprene) molecules are detected ranging from 304 Da (3 isoprene units) to 1664 Da (23 isoprene units), whereas after ethyl acetate extraction, only 8 oligo(cis-1,4-isoprene) molecules are identified ranging from 304 Da (3 isoprene units) to 780 Da (10 isoprene units)
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-
?
cis-1,4-polyisoprene rubber particles + O2
?
the mass distribution of the degradation products differs depending on the extraction solvent. In the presence of pentane, at least 21 oligo(cis-1,4-isoprene) molecules are detected ranging from 304 Da (3 isoprene units) to 1664 Da (23 isoprene units), whereas after ethyl acetate extraction, only 8 oligo(cis-1,4-isoprene) molecules are identified ranging from 304 Da (3 isoprene units) to 780 Da (10 isoprene units)
-
-
?
isoprene rubber particles + O2
oligo(cis-1,4-isoprenoids)
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-
-
-
?
isoprene rubber particles + O2
oligo(cis-1,4-isoprenoids)
-
-
-
-
?
poly(cis-1,4-isoprene) + O2
?
the enzyme degrades poly(1,4-cis-isoprene) to a mixture of oligoisoprene molecules with terminal keto and aldehyde groups
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-
?
poly(cis-1,4-isoprene) + O2
?
the enzyme degrades poly(1,4-cis-isoprene) to a mixture of oligoisoprene molecules with terminal keto and aldehyde groups
-
-
?
polyisoprene latex milk + O2
?
polyisoprene latex milk with an average molecular weight Mn of the polyisoprene of 400,000 g/mol
-
-
?
polyisoprene latex milk + O2
?
polyisoprene latex milk with an average molecular weight Mn of the polyisoprene of 400,000 g/mol
-
-
?
rubber + O2
?
-
RoxB cleaves rubber in an endotype reaction
-
-
?
trans-1,4-polyisoprene + n O2
?
-
the enzyme produces cis-oligo-isoprenoid molecules of n = 2 (231 g/mol) and n = 4 (299 g/mol) where n is equal to the number of isoprene units of the oligo-isoprenoid molecules
-
-
?
trans-1,4-polyisoprene + n O2
?
-
the enzyme produces cis-oligo-isoprenoid molecules of n = 2 (231 g/mol) and n = 4 (299 g/mol) where n is equal to the number of isoprene units of the oligo-isoprenoid molecules
-
-
?
additional information
?
-
-
the enzyme has no peroxidase activity
-
-
-
additional information
?
-
-
the enzyme has no peroxidase activity
-
-
-
additional information
?
-
-
the enzyme has no peroxidase activity
-
-
-
additional information
?
-
-
the enzyme has no peroxidase activity
-
-
-
additional information
?
-
-
the enzyme degrades UV-oxidized polyolefin plastics (polyethylene, polypropylene, and polystyrene)
-
-
-
additional information
?
-
-
the enzyme has no peroxidase activity
-
-
-
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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
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
Nocardia farcinica NVL3
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves cis-1,4-polyisoprene to a mixture of C20 and higher oligoisoprenoids
-
-
?
cis-1,4-polyisoprene + n O2
?
Solimonas fluminis HR-BB
-
the enzyme cleaves cis-1,4-polyisoprene to a mixture of C20 and higher oligoisoprenoids
-
-
?
cis-1,4-polyisoprene + n O2
?
-
the enzyme cleaves polyisoprene randomly to a mixture of oligoisoprenoids (C20 to around C65 oligoisoprenoids) with terminal keto and aldehyde group
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
?
the enzyme produces a mixture of oligo-isoprenoids (C20, C25, C30 and higher oligo-isoprenoids)
-
-
?
cis-1,4-polyisoprene + n O2
n (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
-
-
-
?
cis-1,4-polyisoprene + n O2
n (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
-
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is essential for the microbial utilization of rubber
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is essential for the microbial utilization of rubber
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is involved in rubber degradation
-
-
?
cis-1,4-polyisoprene + O2
?
-
the enzyme is involved in rubber degradation
-
-
?
cis-1,4-polyisoprene + O2
?
Nocardia farcinica DSM 43665T
the enzyme is involved in rubber degradation
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is involved in rubber degradation
-
-
?
cis-1,4-polyisoprene + O2
?
-
Gram-negative rubber-degrading bacteria generally utilise two synergistically acting rubber oxygenases (RoxA/RoxB) for efficient cleavage of polyisoprene to (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
-
-
?
cis-1,4-polyisoprene + O2
?
-
Gram-negative rubber-degrading bacteria generally utilise two synergistically acting rubber oxygenases (RoxA/RoxB) for efficient cleavage of polyisoprene to (4Z,8Z)-4,8-dimethyl-12-oxotrideca-4,8-dienal
-
-
?
cis-1,4-polyisoprene + O2
?
the enzyme is involved in the initial cleavage of poly(cis-1,4-isoprene)
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome
b-type cytochrome. The haem group of LcpK30 is ligated to the polypeptide by a proximal histidine (His198) and by a lysine residue (Lys167) as the distal axial ligand
-
additional information
no indication for the presence of iron, other metals, or cofactors in Lcp
-
heme
presence of 2 c-type hemes, presence of two c-type heme binding motifs (C192HAC195H and C391ASC394H)
heme
2 c-type hemes. Both heme sites of RoxB are present in an oxidized Fe3+ form
heme
presence of one b-type haem in LcpRr as a co-factor is confirmed by metal analysis, solvent extraction, bipyridyl assay and detection of haem-b specific m/z values via mass-spectrometry
heme
-
b-heme-containing protein with an oxidized, 5fold coordinated (open) heme centre
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
no indication for the presence of iron, other metals, or cofactors in Lcp
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE