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Literature summary for 3.1.8.1 extracted from

  • Huang, L.F.; Su, B.; Jao, S.C.; Liu, K.T.; Li, W.S.
    Aminopeptidase P mediated detoxification of organophosphonate analogues of sarin: mechanistic and stereochemical study at the phosphorus atom of the substrate (2006), Chembiochem, 7, 506-514.
    View publication on PubMed
Search for more literature for 3.1.8.1

Protein Variants

Protein Variants Comment Organism
R153A prefers the formation of (S)-O-methyl-methylphosphonothionic acid over the (R)-enantiomer Escherichia coli
R153L/R370L prefers the formation of (S)-O-methyl-methylphosphonothionic acid over the (R)-enantiomer Escherichia coli
R153W/R370L hydrolyses the (S)-enantiomer of O-methoxy-p-nitrophenyl methylphosphonate significantly faster than the (R)-isomer. Prefers the formation of (S)-O-methyl-methylphosphonothionic acid over the (R)-enantiomer Escherichia coli
R370L prefers the formation of (S)-O-methyl-methylphosphonothionic acid over the (R)-enantiomer Escherichia coli
W88L prefers the formation of (S)-O-methyl-methylphosphonothionic acid over the (R)-enantiomer Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Reaction

Reaction Comment Organism Reaction ID
an aryl dialkyl phosphate + H2O = dialkyl phosphate + an aryl alcohol catalytic reaction with orpanophosphonates starts with cleavageof the P-O bond. Reaction proceeds through a displacement mechanism and generates a chiral product in situ with an inversion of stereochemical configuration at the phosphorous atom Escherichia coli
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-nitrophenyl phenyl methylphosphonate + H2O wild-type, 78% of the activity with propyl 4-nitrophenyl methylphosphonate Escherichia coli phenyl hydrogen methylphosphonate + 4-nitrophenol
-
 ?
4-nitrophenyl propan-2-yl methylphosphonate + H2O wild-type, 57% of the activity with propyl 4-nitrophenyl methylphosphonate Escherichia coli propan-2-yl hydrogen methylphosphonate + 4-nitrophenol
-
 ?
butan-2-yl 4-nitrophenyl methylphosphonate + H2O wild-type, 50% of the activity with propyl 4-nitrophenyl methylphosphonate Escherichia coli butan-2-yl hydrogen methylphosphonate + 4-nitrophenol
-
 ?
ethyl 4-nitrophenyl methylphosphonate + H2O wild-type, 50% of the activity with propyl 4-nitrophenyl methylphosphonate Escherichia coli ethyl hydrogen methylphosphonate + 4-nitrophenol
-
 ?
methyl 4-nitrophenyl methylphosphonate + H2O wild-type, 733% of the activity with propyl 4-nitrophenyl methylphosphonate Escherichia coli methyl hydrogen methylphosphonate + 4-nitrophenol
-
 ?
O,O-diisopropyl-4-nitrophenyl phosphate + H2O
-
 Escherichia coli dipropan-2-yl hydrogen phosphate + 4-nitrophenol
-
 ?
O-methyl O-(4-nitrophenyl) methylphosphonothioate + H2O
-
 Escherichia coli O-methyl-methylphosphonothionic acid + 4-nitrophenol
-
 ?
propyl 4-nitrophenyl methylphosphonate + H2O
-
 Escherichia coli propyl hydrogen methylphosphonate + 4-nitrophenol
-
 ?