1.21.3.1: isopenicillin-N synthase
This is an abbreviated version!
For detailed information about isopenicillin-N synthase, go to the full flat file.
Word Map on EC 1.21.3.1
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1.21.3.1
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chrysogenum
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acremonium
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penicillium
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beta-lactam
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tripeptide
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cephalosporium
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nidulans
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clavuligerus
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delta-l-alpha-aminoadipoyl-l-cysteinyl-d-valine
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deacetoxycephalosporin
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pcbab
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cephamycins
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jumonjinensis
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thiazolidine
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cipns
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lld-acv
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penams
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lactamdurans
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non-haem
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daocs
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biotechnology
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synthesis
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pharmacology
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medicine
- 1.21.3.1
- chrysogenum
- acremonium
- penicillium
- beta-lactam
- tripeptide
- cephalosporium
- nidulans
- clavuligerus
- delta-l-alpha-aminoadipoyl-l-cysteinyl-d-valine
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deacetoxycephalosporin
-
pcbab
-
cephamycins
- jumonjinensis
- thiazolidine
-
cipns
-
lld-acv
-
penams
- lactamdurans
-
non-haem
- daocs
- biotechnology
- synthesis
- pharmacology
- medicine
Reaction
Synonyms
IPN cyclase, IPN synthase, IPNS, isopenicillin N synthase, isopenicillin N synthase (cyclase), isopenicillin N synthetase, isopenicillin N-synthase, isopenicillin-N synthase, isopenicillin-N-synthase, More, PcbC, synthetase, isopenicillin N (9Cl)
ECTree
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Reaction
Reaction on EC 1.21.3.1 - isopenicillin-N synthase
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structure and mechanism
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
structure and mechanism
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
structure and mechanism
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
structure and mechanism
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
structure and mechanism
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
ligation of substrate to the iron centre
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
active site with conserved jelly-roll motif, cysteine residues are not directly involved in the coordination of the metal ion
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
Cys106 is involved in substrate binding, Cys255 is involved in maintaining the protein structure
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
removal of 4 hydrogen atoms to form the 4-membered beta-lactam and the 5-membered thiazolidine ring
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
removal of 4 hydrogen atoms to form the 4-membered beta-lactam and the 5-membered thiazolidine ring
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
removal of 4 hydrogen atoms to form the 4-membered beta-lactam and the 5-membered thiazolidine ring
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
catalytic reaction is under steric regulation
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
radical pathway, analogous to the first step of a radicalbased hydroxylation reaction
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
isopenicillin-N synthase is the main rate-limiting enzyme for penicillin-G biosynthesis
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N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
the hydroperoxide-ferrous intermediate, formed by O2-activated H atom abstraction from the substrate, can exploit different reaction pathways and interactions with the substrate govern the final pathway
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