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1.14.20.1: deacetoxycephalosporin-C synthase

This is an abbreviated version!
For detailed information about deacetoxycephalosporin-C synthase, go to the full flat file.

Word Map on EC 1.14.20.1

Reaction

Penicillin N
+
2-oxoglutarate
+
O2
=
deacetoxycephalosporin C
+
succinate
+
CO2
+
H2O

Synonyms

acDAOC/DACS, cefE, cefEF, Cephalosporin biosynthesis expandase/hydroxylase, DAOC synthase, DAOC/DAC synthase, DAOC/DACS, DAOCS, deacetoxy/deacetylcephalosporin C synthase, deacetoxycephalosporin C synthase, deacetoxycephalosporin-C synthase, deacetoxycephalosporin-C synthetase, deacetoxycephalosporin/deacetylcephalosporin C synthase, expandase, expendase, penicillin N expandase, scDAOCS

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.20 With 2-oxoglutarate as one donor, and the other dehydrogenated
                1.14.20.1 deacetoxycephalosporin-C synthase

Substrates Products

Substrates Products on EC 1.14.20.1 - deacetoxycephalosporin-C synthase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(thiophen-2-ylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid + 2-oxoglutarate + O2
(6R,7R)-3-methyl-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
3-exomethylenecephalosporin C + 2-oxoglutarate + O2
deacetylcephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
8% of the activity with cephalosporin N, recombinant enzyme
-
?
6-alpha-methylpenicillin N + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
6-aminopenicillanic acid + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
7-aminodeacetoxycephalosporanic acid + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
low activity, hydroxylation reaction
-
-
ir
acetyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-acetylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
acetyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-adipylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
amoxicillin + 2-oxoglutarate + O2
?
show the reaction diagram
amoxicillin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
ampicillin + 2-oxo-4-methyl-pentanoic acid + O2
?
show the reaction diagram
mutants R258H, R258K, R258Q, R258A, R258L, R258F, no activity with the wild-type enzyme
-
-
ir
ampicillin + 2-oxo-4-methylpentanoate + O2
cephalexin + succinate + CO2 + H2O
show the reaction diagram
wild-type enzyme has a requirement for 2-oxoglutarate and cannot efficiently use hydrophobic 2-oxoacids, the mutants R258A, R258L, R258H and R258F have broadened cosubstrate selectivity and are able to utilize hydrophobic 2-oxoacids
-
?
ampicillin + 2-oxoglutarate + O2
?
show the reaction diagram
ampicillin + 2-oxoglutarate + O2
? + succinate + CO2
show the reaction diagram
ampicillin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
ampicillin + 2-oxoglutarate + O2
cephalexin + succinate + CO2 + H2O
show the reaction diagram
ampicillin + 2-oxohexanoate + O2
cephalexin + ?
show the reaction diagram
wild-type enzyme has a requirement for 2-oxoglutarate and cannot efficiently use hydrophobic 2-oxoacids, the mutants R258A, R258L, R258H and R258F have broadened cosubstrate selectivity and are able to utilize hydrophobic 2-oxoacids
-
-
?
ampicillin + 2-oxohexanoic acid + O2
?
show the reaction diagram
mutants R258H, R258K, R258Q, R258A, R258L, R258F, no activity with the wild-type enzyme
-
-
ir
butyryl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-butyrylaminocephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
carbenicillin + 2-oxoglutarate + O2
?
show the reaction diagram
carbenicillin + 2-oxoglutarate + O2
? + succinate + CO2
show the reaction diagram
carbenicillin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
cephalexin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
low activity, hydroxylation reaction
-
-
ir
D-carboxymethylcysteinyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
?
show the reaction diagram
-
-
-
?
deacetoxycephalosporin C + 2-oxoglutarate + O2
deacetylcephalosporin C + succinate + CO2
show the reaction diagram
deacetoxycephalosporin C + 2-oxoglutarate + O2
deacetylcephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
-
?
decanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-decanoylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
heptanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-heptanoylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
hexanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-hexanoylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
metampicillin + 2-oxoglutarate + O2
?
show the reaction diagram
metampicillin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
N-((thiophen-2-yl)acetyl)-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-[(5R,6R)-3,3-dimethyl-2,7-dioxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]-2-(thiophen-2-yl)acetamide + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-acetyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-acetyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-adipyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
N-butyryl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-butyryldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-decanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-decanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-heptanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-heptanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-hexanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-hexanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-nonanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-nonanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-nonanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-nonanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-octanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-octanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-octanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-octanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-valeryl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N-valeryldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
N-valeryl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-pentanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
penicillin F + 2-oxoglutarate + O2
7-((3E)-hex-3-enoyl)aminocephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
penicillin G + 2-oxo-4-methyl-pentanoic acid + O2
phenylacetyl-7-aminodeacetoxycephalosporanic acid + 3-methylbutanoate + CO2 + H2O
show the reaction diagram
mutants R258H, R258K, R258Q, R258A, R258L, R258F, no activity with the wild-type enzyme
-
-
ir
penicillin G + 2-oxo-4-methylpentanoate + O2
phenylacetyl-7-aminodeacetoxy cephalosporanic acid + ?
show the reaction diagram
penicillin G + 2-oxoglutarate + O2
7-phenylacetylaminocephalosporanate + succinate + CO2 + H2O
show the reaction diagram
penicillin G + 2-oxoglutarate + O2
7-phenylacetylaminocephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
low catalytic effciency towards penicillin G
-
-
?
penicillin G + 2-oxoglutarate + O2
? + succinate + CO2
show the reaction diagram
penicillin G + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
penicillin G + 2-oxoglutarate + O2
phenylacetyl-7-aminodeacetoxy cephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
penicillin G + 2-oxoglutarate + O2
phenylacetyl-7-aminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
penicillin G + 2-oxohexanoate + O2
phenylacetyl-7-aminodeacetoxy cephalosporanic acid + ?
show the reaction diagram
penicillin G + 2-oxohexanoic acid + O2
phenylacetyl-7-aminodeacetoxycephalosporanic acid + pentanoate + CO2 + H2O
show the reaction diagram
mutants R258H, R258K, R258Q, R258A, R258L, R258F, no activity with the wild-type enzyme
-
-
ir
penicillin mX + 2-oxoglutarate + O2
7-[(3-hydroxyphenyl)acetyl]aminocephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
show the reaction diagram
penicillin V + 2-oxoglutarate + O2
?
show the reaction diagram
penicillin V + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
penicillin X + 2-oxoglutarate + O2
7-[(4-hydroxyphenyl)acetyl]aminocephalosporanic acid + succinate + CO2 + H2O
show the reaction diagram
-
-
-
?
phenethicillin + 2-oxoglutarate + O2
?
show the reaction diagram
phenethicillin + 2-oxoglutarate + O2
? + succinate + CO2
show the reaction diagram
phenethicillin + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
phenyl-7-aminodeacetoxycephalosporanic acid + 2-oxoglutarate + O2
? + succinate + CO2 + H2O
show the reaction diagram
hydroxylation reaction
-
-
ir
ticarcillin + 2-oxoglutarate + O2
?
show the reaction diagram
-
-
-
?
additional information
?
-