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
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1.14.20.1
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clavuligerus
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chrysogenum
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acremonium
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isopenicillin
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penicillium
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beta-lactams
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epimerase
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cephamycins
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cephalosporium
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ring-expansion
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7-aminodeacetoxycephalosporanic
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pcbab
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ironii
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cephem
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lactamdurans
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synthesis
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7-adca
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2-oxoglutarate-dependent
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cephalexin
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carbenicillin
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doacs
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biotechnology
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medicine
- 1.14.20.1
- clavuligerus
- chrysogenum
- acremonium
- isopenicillin
- penicillium
- beta-lactams
-
epimerase
-
cephamycins
- cephalosporium
-
ring-expansion
-
7-aminodeacetoxycephalosporanic
-
pcbab
-
ironii
-
cephem
- lactamdurans
- synthesis
-
7-adca
-
2-oxoglutarate-dependent
- cephalexin
- carbenicillin
-
doacs
- biotechnology
- medicine
Reaction
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
1.14.20.1 deacetoxycephalosporin-C synthaseAdvanced search results
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results (Natural Substrates Products
Natural Substrates Products on EC 1.14.20.1 - deacetoxycephalosporin-C synthase
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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
(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
-
-
-
?
acetyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-acetylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-adipylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
butyryl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-butyrylaminocephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
D-carboxymethylcysteinyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
?
-
-
-
?
deacetoxycephalosporin C + 2-oxoglutarate + O2
deacetylcephalosporin C + succinate + CO2 + H2O
-
-
-
-
?
decanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-decanoylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
heptanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-heptanoylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
hexanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-hexanoylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
N-nonanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-nonanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
N-octanoyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-octanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
N-valeryl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-pentanoyldeacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin F + 2-oxoglutarate + O2
7-((3E)-hex-3-enoyl)aminocephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
penicillin G + 2-oxoglutarate + O2
7-phenylacetylaminocephalosporanic acid + succinate + CO2 + H2O
low catalytic effciency towards penicillin G
-
-
?
penicillin G + 2-oxoglutarate + O2
phenylacetyl-7-aminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
penicillin mX + 2-oxoglutarate + O2
7-[(3-hydroxyphenyl)acetyl]aminocephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
penicillin X + 2-oxoglutarate + O2
7-[(4-hydroxyphenyl)acetyl]aminocephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-adipylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
7-adipylaminodesacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
deacetoxycephalosporin C + 2-oxoglutarate + O2
deacetylcephalosporin C + succinate + CO2
-
-
-
ir
deacetoxycephalosporin C + 2-oxoglutarate + O2
deacetylcephalosporin C + succinate + CO2
-
-
-
ir
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
-
?
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
-
?
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
-
?
N-adipyl-6-aminopenicillanic acid + 2-oxoglutarate + O2
N7-adipylaminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
-
?
penicillin G + 2-oxoglutarate + O2
phenylacetyl-7-aminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
-
?
penicillin G + 2-oxoglutarate + O2
phenylacetyl-7-aminodeacetoxycephalosporanic acid + succinate + CO2 + H2O
-
-
product is the precursor of 7-aminodeacetoxycephalosporanic acid, which is used in industrial applications
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ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
ring expansion of penicillin N to a six member cephem ring, the natural enzyme is only able to use 2-oxoglutarate but not 2-oxobutyrate, 3-oxoadipate, 2-oxohexanoic acid or 2-oxo-4-methylpentanoic acid as cosubstrates
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
-
ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
the enzyme catalyzes the committed step in the biosynthesis of cephalosporin antibiotics
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
committed step in biosynthesis of cephamycin C
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
the enzyme is involved in catalyzing the biosynthesis of cephalosporins and cephamycin
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
first step in cephamycin C biosynthetic pathway
-
-
ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
key step in the cephamycin C biosynthesis pathway, the ring expansion step by incorporation of a methyl group into the cephem ring
-
-
ir
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
the enzyme catalyzes the ring expansion of penicillin substrates into a ring-expanded product to eventually produce cephamycin C
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
the enzyme catalyzes the ring expansion of penicillin substrates into a ring-expanded product to produce cephamycin C
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
the enzyme catalyzes the ring expansion of penicillin substrates into a ring-expanded product to eventually produce cephamycin C
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
-
-
-
?
penicillin N + 2-oxoglutarate + O2
deacetoxycephalosporin C + succinate + CO2 + H2O
first step in cephamycin C biosynthetic pathway
-
-
ir
additional information
?
-
-
the enzyme catalyzes the first and second step in the cephamycin C biosynthetic pathway
-
-
?
additional information
?
-
the enzyme catalyzes the first and second step in the cephamycin C biosynthetic pathway
-
-
?
additional information
?
-
-
a bifunctional enzyme that catalyzes both the ring-expansion of penicillin N to deacetoxycephalosporin C and the hydroxylation of the latter to deacetylcephalosporin C
-
-
?
additional information
?
-
-
does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates
-
-
?
additional information
?
-
-
does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates
-
-
?
additional information
?
-
-
does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates
-
-
?
additional information
?
-
enzyme is able to convert a wide range of penicillin substrates differing in their side chains, it is a member of 2-oxoglutarate-dependent dioxygenase protein family, the mechanism involves initial activation of the iron centre by 2-oxoglutarate binding followed by oxidative decarboxylation of 2-oxoglutarate to generate oxidizing ferryl species with succinate and carbon dioxide as by-products, succinate remains bound and stabilizes the reactive iron species until the substrate enters the active site, binding of penicillin to the reactive iron species via the sulfur group subsequently expels succinate and leads to oxidative ring expansion of the substrate
-
-
?
additional information
?
-
-
enzyme is able to convert a wide range of penicillin substrates differing in their side chains, it is a member of 2-oxoglutarate-dependent dioxygenase protein family, the mechanism involves initial activation of the iron centre by 2-oxoglutarate binding followed by oxidative decarboxylation of 2-oxoglutarate to generate oxidizing ferryl species with succinate and carbon dioxide as by-products, succinate remains bound and stabilizes the reactive iron species until the substrate enters the active site, binding of penicillin to the reactive iron species via the sulfur group subsequently expels succinate and leads to oxidative ring expansion of the substrate
-
-
?
additional information
?
-
-
Streptomyces clavuligerus deacetoxycephalosporin C synthase is an iron- and 2-ketoglutarate-dependent oxidase, with the ability to catalyze the ring expansion reaction of penicillins, which converts the thiazolidine ring in penicillins to the dihydrothiazine ring. scDAOCS converts its natural substrate, penicillin N, whereas it has very low activity on the bulk and cheap penicillins such as penicillin G
-
-
?
additional information
?
-
-
Streptomyces clavuligerus deacetoxycephalosporin C synthase is an iron- and 2-ketoglutarate-dependent oxidase, with the ability to catalyze the ring expansion reaction of penicillins, which converts the thiazolidine ring in penicillins to the dihydrothiazine ring. scDAOCS converts its natural substrate, penicillin N, whereas it has very low activity on the bulk and cheap penicillins such as penicillin G
-
-
?
additional information
?
-
-
does not use isopenicillin N or 6-aminopenicillanic acid as substrates, the natural enzyme is only able to use 2-oxoglutarate but not 2-ketobutyrate, 3-ketoadipate, 2-ketohexanoic acid, or 2-keto-4-methylpentanoic acid as cosubstrates
-
-
?
additional information
?
-
enzyme is able to convert a wide range of penicillin substrates differing in their side chains, it is a member of 2-oxoglutarate-dependent dioxygenase protein family, the mechanism involves initial activation of the iron centre by 2-oxoglutarate binding followed by oxidative decarboxylation of 2-oxoglutarate to generate oxidizing ferryl species with succinate and carbon dioxide as by-products, succinate remains bound and stabilizes the reactive iron species until the substrate enters the active site, binding of penicillin to the reactive iron species via the sulfur group subsequently expels succinate and leads to oxidative ring expansion of the substrate
-
-
?
