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diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
the enzyme exhibits stereoselectivity toward the hydrolysis of chiral substrates with a preference for the S-P enantiomers
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
catalytic mechanism, H287 is required for catalytic activity
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
enzyme exhibits stereoselectivity toward the chiral phosphorus center of the p-nitrophenyl analogs of sarin and soman
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
squide-type enzyme: diisopropyl fluorophosphate hydrolysed more rapidly than soman, Mazur-type enzyme: soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
squide-type enzyme: diisopropyl fluorophosphate hydrolysed more rapidly than soman, Mazur-type enzyme: soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
squide-type enzyme: diisopropyl fluorophosphate hydrolysed more rapidly than soman, Mazur-type enzyme: soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
squide-type enzyme: diisopropyl fluorophosphate hydrolysed more rapidly than soman, Mazur-type enzyme: soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
squide-type enzyme: diisopropyl fluorophosphate hydrolysed more rapidly than soman, Mazur-type enzyme: soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
squide-type enzyme: diisopropyl fluorophosphate hydrolysed more rapidly than soman, Mazur-type enzyme: soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
calcium coordinating residue D229, in concert with direct substrate activation by the metal ion, renders the phosphorus atom of the substrate susceptible for attack of water, through generation of a phosphoenzyme intermediate
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
analysis of the catalytic reaction mechanism of the enzyme. Proposed mechanism for phosphoenzyme intermediate formation involving Asp229 as the nucleophile. (i) Asp229 attacks the phosphorus center of DFP to form a pentavalent intermediate and (ii) the P-F bond dissociates to form a tetrahedral phosphoenzyme intermediate. Hydrolysis of the phosphoenzyme intermediate is not shown. And proposed mechanism for hydrolysis involving an activated water as the nucleophile. (i) Asp229 abstracts a proton from a water molecule either stepwise or in concert as (ii) water attacks the phosphorus center, (iii) Glu21 abstracts a proton either stepwise or in concert as water forms a bond with phosphorus, and (iv) the P-F bond dissociates
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
catalytic reaction mechanism involving residue Asp269, molecular dynamics and modelling, overview
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
molecular details of the catalytic mechanism of h-PON1
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
the catalytic mechanism of DFPase is investigated using the hybrid density functional theory method B3LYP with a large quantum chemical model of the active site abstracted from the X-ray crystal structure. For the first step, two different pathways are considered: (1) residue Asp229 as a nucleophile inline attacks on the phosphorus center and (2) an activated water molecule as the nucleophile attacks on the phosphorus center. Both the Asp229 and the activated water molecule are capable of proceeding nucleophilic attack on the substrate in the presence of Ca2+ ion with the associated barriers 14.8 and 6.0 kcal/mol, respectively. The latter is much easier to perform the nucleophile attack. From the phosphoenzyme intermediate with the hexa-coordinated Ca2+, the uncoordinated Glu21 functions as a general base activated an additional water molecule to attack the carbon center of Asp229 and make the phosphate release. Residues Asn120 and Asn175 promote the elimination of the fluoride via donating strong hydrogen bonds. Residue Asp229 plays a dual role during the hydrolysis reaction process, either as a nucleophile or as a general base to activate the water nucleophile. The role of the calcium ion is providing a necessary conformation of the active site, facilitating the nucleophile formation and substrate orientation
diisopropyl fluorophosphate + H2O = diisopropyl phosphate + fluoride
-
-
-
-
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(R)-cyclosarin + H2O
?
-
-
-
?
(R)-sarin + H2O
?
-
-
-
?
(RS)-propan-2-yl methylphosphonofluoridate + H2O
isopropyl phosphate methylphosphonate + fluoride
(RS)-propan-2-yl methylphosphonofluoridate + H2O
propan-2-yl methylphosphonate + fluoride
i.e. sarin
-
-
?
(S)-cyclosarin + H2O
?
-
-
-
?
1,2,2-trimethylpropyl methylphosphonofluoridoate + H2O
1,2,2-trimethylpropyl methylphosphonate + fluoride + H+
-
-
-
?
1-methylethyl methylphosphonofluoridoate + H2O
1-methylethyl methylphosphonate + fluoride + H+
-
-
-
?
3-[fluoro(methyl)phosphoryl]oxy-2,2-dimethylbutane + H2O
3,3-dimethylbutan-2-yl methylphosphonate + fluoride
3-[fluoro(methyl)phosphoryl]oxy-2,2-dimethylbutane + H2O
Pinacolyl methylphosphonate + fluoride
i.e. soman
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
4-nitrophenyl-methyl(phenyl)phosphinate + H2O
?
4-nitrophenylisopropyl phenylphosphinate + H2O
?
-
at 22% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
4-nitrophenylpropyl phenylphosphinate + H2O
?
-
at 24% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
chlorpyrifos + H2O
?
-
-
-
?
chlorpyrifos oxon + H2O
diethyl phosphate + 3,5,6-trichloropyridin-2-ol
coumaphos + H2O
?
-
-
-
-
?
cyclohexyl methyl fluorophosphate + H2O
cyclohexyl methyl hydrogen phosphate + fluoride
cyclohexyl methylphosphonofluoridate + H2O
cyclohexyl methylphosphonate + fluoride
i.e. cyclosarin
-
-
?
cyclohexyl methylphosphonofluoridoate + H2O
cyclohexyl methylphosphonate + fluoride + H+
-
-
-
?
cyclohexylmethylphosphonofluoridate + H2O
cyclohexyl methylphosphonate + fluoride
i.e. cyclosarin
-
-
?
cyclohexylsarin + H2O
?
-
-
-
-
?
diazinon + H2O
?
-
-
-
-
?
diethyl fluorophosphate + H2O
diethyl phosphate + fluoride
-
-
-
?
diethyl-paraoxon + H2O
diethyl phosphate + 4-nitrophenol
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
diisopropyl phosphofluoridate + H2O
diisopropyl phosphate + fluoride
diisopropyl phosphorofluoridate + H2O
diisopropyl phosphate + fluoride
ethyl dimethylamidocyanophosphate + H2O
ethyl hydrogen dimethylphosphoramidate + HCN
-
-
-
?
ethyl dimethylphosphoramidocyanidate + H2O
?
ethyl dimethylphosphoramidocyanidate + H2O
ethyl hydrogen dimethylphosphoramidate + HCN
i.e. tabun
-
-
?
ethyl N,N-dimethylphosphoramidocyanidate + H2O
ethyl N,N-dimethylphosphoramide + cyanide
-
i.e. tabun
-
-
?
fensulfothion + H2O
?
-
-
-
-
?
methyl parathion + H2O
?
-
-
-
-
?
mipafox + H2O
?
-
i.e. N,N'-diisopropyl phosphorodiamidofluoridate, poor substrate
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphate + fluoride
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphonate + fluoride
O-cyclohexylmethylphosphonofluoridate + H2O
?
O-ethyl S-(2-diisopropylamino)ethyl methylphosphonothioate + H2O
?
-
an organophosphorous nerve agent
-
-
?
O-isopropylmethylphosphonofluoridate + H2O
O-isopropylmethylphosphate + fluoride
O-pinacolyl methylphosphonofluoridate + H2O
O-pinacolyl methylphosphate + fluoride
O-pinacolylmethylphosphonofluoridate + H2O
?
-
best substrate
-
-
?
p-nitrophenyl-soman + H2O
p-nitrophenol + soman
paraoxon + H2O
diethylphosphate + 4-nitrophenol
parathion + H2O
?
-
-
-
-
?
phenyl acetate + H2O
phenol + acetate
additional information
?
-
(RS)-propan-2-yl methylphosphonofluoridate + H2O
isopropyl phosphate methylphosphonate + fluoride
i.e. sarin
-
-
?
(RS)-propan-2-yl methylphosphonofluoridate + H2O
isopropyl phosphate methylphosphonate + fluoride
i.e. sarin
-
-
?
(S)-sarin + H2O
?
-
-
-
?
(S)-sarin + H2O
?
-
the calculated free energy barrier for hydrolysis of (S)-sarin by the mechanism for diiisopropyl fluorophosphate is highly unfavorable. Hydrolysis of (S)-sarin proceeds by a mechanism in which Asp229 could activate an intervening water molecule for nucleophilic attack on the substrate
-
?
3-[fluoro(methyl)phosphoryl]oxy-2,2-dimethylbutane + H2O
3,3-dimethylbutan-2-yl methylphosphonate + fluoride
i.e. soman
-
-
?
3-[fluoro(methyl)phosphoryl]oxy-2,2-dimethylbutane + H2O
3,3-dimethylbutan-2-yl methylphosphonate + fluoride
i.e. soman
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
-
40% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
-
i.e. 4-nitrophenylethyl phenylphosphinate
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
-
at 46% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
-
Rangia cuneata (Mazur-type enzyme): better substrate than diisopropyl fluorophosphate
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
-
i.e. NPEPP
-
-
?
4-nitrophenyl-ethyl(phenyl)phosphinate + H2O
?
-
i.e. NPEPP
-
-
?
4-nitrophenyl-methyl(phenyl)phosphinate + H2O
?
-
at 49% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
4-nitrophenyl-methyl(phenyl)phosphinate + H2O
?
-
i.e. 4-nitrophenylmethyl phenylphosphinate
-
-
?
4-nitrophenyl-methyl(phenyl)phosphinate + H2O
?
-
at 28% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
chlorpyrifos oxon + H2O
diethyl phosphate + 3,5,6-trichloropyridin-2-ol
-
-
-
?
chlorpyrifos oxon + H2O
diethyl phosphate + 3,5,6-trichloropyridin-2-ol
i.e. CPO, a metabolite of chlorpyrifos that is used as a pesticide in agriculture industry
-
-
?
cyclohexyl methyl fluorophosphate + H2O
cyclohexyl methyl hydrogen phosphate + fluoride
-
(+)isomer, pH 7.2, 1 mM MnCl2
-
-
?
cyclohexyl methyl fluorophosphate + H2O
cyclohexyl methyl hydrogen phosphate + fluoride
-
(+)isomer, pH 7.2, 1 mM MnCl2
-
-
?
cyclohexyl methyl fluorophosphate + H2O
cyclohexyl methyl hydrogen phosphate + fluoride
-
(+)isomer, pH 7.2, 1 mM MnCl2
-
-
?
cyclosarin + H2O
?
-
-
-
-
?
cyclosarin + H2O
?
-
-
-
?
diethyl-paraoxon + H2O
diethyl phosphate + 4-nitrophenol
reaction of EC 3.1.8.1
-
-
?
diethyl-paraoxon + H2O
diethyl phosphate + 4-nitrophenol
reaction of EC 3.1.8.1, paraoxonase
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
soman hydrolysed more rapidly than diisopropyl fluorophosphate
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
highly toxic structural analogue of G-class type of nerve agents
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
spectrophotometric determination with phenol red
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
best substrate of squid enzyme
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
The mechanism for hydrolysis of diisopropyl fluorophosphate involves nucleophilic attack by Asp229 on phosphorus to form a pentavalent intermediate. P-F bond dissociation then yields a phosphoacyl enzyme intermediate in the rate-limiting step. A water molecule, coordinated to the catalytic Ca2+, donates a proton to Asp121 and then attacks the tetrahedral phosphoacyl intermediate to liberate the diisopropyl phosphate product
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
room temperature, pH 7.5
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
at about 30% of O-pinacolylmethylphosphonofluoridate hydrolysis
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
binding analysis, overview
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
at about 5-10% of soman hydrolysis
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
an analogue molecule of G-type warfare agents
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. O,O-diisopropyl phosphorofluoridate
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
i.e. DFP
-
-
?
diisopropyl fluorophosphate + H2O
diisopropyl phosphate + fluoride
-
-
-
-
?
diisopropyl phosphofluoridate + H2O
diisopropyl phosphate + fluoride
-
SMP30 is important in diisopropyl phosphofluoridate detoxification
-
-
?
diisopropyl phosphofluoridate + H2O
diisopropyl phosphate + fluoride
-
substrate of SMP30
-
-
?
diisopropyl phosphofluoridate + H2O
diisopropyl phosphate + fluoride
-
-
-
?
diisopropyl phosphofluoridate + H2O
diisopropyl phosphate + fluoride
SMP30 is important in diisopropyl phosphofluoridate detoxification
-
-
?
diisopropyl phosphorofluoridate + H2O
diisopropyl phosphate + fluoride
-
pH 8.0, 25°C, 1 mM MgCl2
-
-
?
diisopropyl phosphorofluoridate + H2O
diisopropyl phosphate + fluoride
pH 8.0, 25°C, 1 mM MgCl2
-
-
?
ethyl dimethylphosphoramidocyanidate + H2O
?
i.e. tabun
-
-
?
ethyl dimethylphosphoramidocyanidate + H2O
?
i.e. tabun
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphate + fluoride
-
i.e. cyclosarin
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphate + fluoride
-
i.e. cyclosarin
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphate + fluoride
-
i.e. cyclosarin
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphonate + fluoride
-
no reaction with the (-)isomer O-cyclohexyl methylphosphonofluoridate
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphonate + fluoride
-
no reaction with the (-)isomer O-cyclohexyl methylphosphonofluoridate
-
-
?
O-cyclohexyl methylphosphonofluoridate + H2O
O-cyclohexyl methylphosphonate + fluoride
-
no reaction with the (-)isomer O-cyclohexyl methylphosphonofluoridate
-
-
?
O-cyclohexylmethylphosphonofluoridate + H2O
?
-
i.e. GF
-
-
?
O-cyclohexylmethylphosphonofluoridate + H2O
?
-
at 114% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
O-isopropylmethylphosphonofluoridate + H2O
O-isopropylmethylphosphate + fluoride
-
i.e. sarin
-
-
?
O-isopropylmethylphosphonofluoridate + H2O
O-isopropylmethylphosphate + fluoride
i.e. sarin
-
-
?
O-isopropylmethylphosphonofluoridate + H2O
O-isopropylmethylphosphate + fluoride
-
i.e. sarin
-
-
?
O-isopropylmethylphosphonofluoridate + H2O
O-isopropylmethylphosphate + fluoride
i.e. sarin
-
-
?
O-isopropylmethylphosphonofluoridate + H2O
O-isopropylmethylphosphate + fluoride
-
i.e. sarin
-
-
?
O-pinacolyl methylphosphonofluoridate + H2O
O-pinacolyl methylphosphate + fluoride
-
i.e. soman
-
-
?
O-pinacolyl methylphosphonofluoridate + H2O
O-pinacolyl methylphosphate + fluoride
i.e. soman
-
-
?
O-pinacolyl methylphosphonofluoridate + H2O
O-pinacolyl methylphosphate + fluoride
i.e. soman
-
-
?
O-pinacolyl methylphosphonofluoridate + H2O
O-pinacolyl methylphosphate + fluoride
-
i.e. soman
-
-
?
p-nitrophenyl-soman + H2O
p-nitrophenol + soman
-
the enzyme is immobilized on a photoluminescent porous silicon platform
soman is O-(2,3,3)-trimethylpropyl methylphosphonofluoridate
-
r
p-nitrophenyl-soman + H2O
p-nitrophenol + soman
-
the enzyme is immobilized on a photoluminescent porous silicon platform
soman is O-(2,3,3)-trimethylpropyl methylphosphonofluoridate
-
r
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
-
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
i.e. diethyl-4-nitrophenyl phosphate, poor substrate
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
substrate are also 16 paraoxon analogs
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
-
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
-
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
i.e. diethyl-4-nitrophenyl phosphate, poor substrate
-
-
?
paraoxon + H2O
diethylphosphate + 4-nitrophenol
-
i.e. diethyl-4-nitrophenyl phosphate, poor substrate
-
-
?
phenyl acetate + H2O
phenol + acetate
-
-
-
?
phenyl acetate + H2O
phenol + acetate
-
-
-
?
phenyl acetate + H2O
phenol + acetate
pH 8.0, 25°C, 1 mM MgCl2
-
-
?
sarin + H2O
?
-
-
-
-
?
sarin + H2O
?
-
at 20% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
sarin + H2O
?
-
substrates are also p-nitrophenyl analogs of sarin, the enzyme exhibits a stereoselective preference for the R-P-enantiomers of sarin
-
-
?
sarin + H2O
?
-
i.e. O-isopropylmethylphosphonofluoridate
-
-
?
sarin + H2O
?
-
at 38% the rate of diisopropyl fluorophosphate hydrolysis
-
-
?
sarin + H2O
?
-
i.e. propyl-2-methane-fluorophosphonate
-
-
?
sarin + H2O
?
-
Mazur-type enzyme
-
3.1.8.2 diisopropyl-fluorophosphatase
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