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Information on EC 1.21.3.1 - isopenicillin-N synthase and Organism(s) Penicillium chrysogenum and UniProt Accession P08703

for references in articles please use BRENDA:EC1.21.3.1
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IUBMB Comments
Forms part of the penicillin biosynthesis pathway (for pathway, click here).
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This record set is specific for:
Penicillium chrysogenum
UNIPROT: P08703
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The taxonomic range for the selected organisms is: Penicillium chrysogenum
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
isopenicillin n synthase, isopenicillin n synthetase, isopenicillin n-synthase, isopenicillin-n synthase, ipn synthase, isopenicillin-n-synthase, isopenicillin n synthase (cyclase), more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
isopenicillin-N-synthase
-
isopenicillin N synthase
isopenicillin N synthase (cyclase)
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isopenicillin N synthetase
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-
-
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isopenicillin-N synthase
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synthetase, isopenicillin N (9Cl)
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-
-
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additional information
-
isopenicillin N synthase belongs to a class of non-heme ferrous iron dependent oxidoreductases
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
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oxidation
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-
-
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reduction
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-
-
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oxidative cyclization
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-
SYSTEMATIC NAME
IUBMB Comments
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine:oxygen oxidoreductase (cyclizing)
Forms part of the penicillin biosynthesis pathway (for pathway, click here).
CAS REGISTRY NUMBER
COMMENTARY hide
78642-31-6
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + H2O
show the reaction diagram
-
-
-
?
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + 2 H2O
show the reaction diagram
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
in Penicillium chrysogenum, the enzymes involved in penicillin production are compartmentalized in the cytosol and in microbodies
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-
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + H2O
show the reaction diagram
-
-
-
?
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + 2 H2O
show the reaction diagram
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
-
in Penicillium chrysogenum, the enzymes involved in penicillin production are compartmentalized in the cytosol and in microbodies
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
alpha-aminoadipic(-Cys-Gly)
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bis[alpha-aminoadipic(-Cys-D-chloroalanine)]
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bis[alpha-aminoadipic(-Cys-D-hexafluorovaline)]
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bis[alpha-aminoadipic(-Cys-D-Phe)]
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bis[alpha-aminoadipic(-Cys-D-Trp)]
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bis[alpha-aminoadipic(-Cys-D-Tyr)]
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bis[alpha-aminoadipic(-Cys-DL-hexafluorovaline)]
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bis[alpha-aminoadipic(-Cys-hexafluorovaline)]
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bis[H-Cys-D-Val]
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additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbic acid
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required
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
IPNA_PENCH
331
0
37960
Swiss-Prot
other Location (Reliability: 2)
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
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functional expression in the cytosol of yeast Hansenula polymorpha, best at 25°C or 30°C growth temperature, at 37°C the recombinant protein is not stable, optimization of culture conditions, overview
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
a developed gene regulation model predicts the expression of this rate limiting enzyme based on glucose repression, fast decay of the mRNA encoding for the enzyme as well as the decay of the enzyme itself
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Castro, J.M.; Liras, P.; Laiz, L.; Cortes, J.; Martin, J.F.
Purification and characterization of the isopenicillin N synthase of Streptomyces lactamdurans
J. Gen. Microbiol.
134
133-141
1988
Acremonium chrysogenum, Amycolatopsis lactamdurans, Penicillium chrysogenum
Manually annotated by BRENDA team
Huffman, G.W.; Gesellchen, P.D.; Turner, J.R.; Rothenberger, R.B.; Osborne, H.E.; Miller, F.D.; Chapman, J.L.; Queener, S.W.
Substrate specificity of isopenicillin N synthase
J. Med. Chem.
35
1897-1914
1992
Acremonium chrysogenum, Penicillium chrysogenum
Manually annotated by BRENDA team
Carr, L.G.; Skatrud, P.L.; Scheetz, M.E 2nd.; Queener, S.W.; Ingolia, T.D.
Cloning and expression of the isopenicillin N synthetase from Penicillium chrysogenum
Gene
48
257-266
1986
Penicillium chrysogenum
Manually annotated by BRENDA team
Gidijala, L.; Bovenberg, R.A.; Klaassen, P.; van der Klei, I.J.; Veenhuis, M.; Kiel, J.A.
Production of functionally active Penicillium chrysogenum isopenicillin N synthase in the yeast Hansenula polymorpha
BMC Biotechnol.
8
29
2008
Penicillium chrysogenum
Manually annotated by BRENDA team
Douma, R.D.; Verheijen, P.J.; de Laat, W.T.; Heijnen, J.J.; van Gulik, W.M.
Dynamic gene expression regulation model for growth and penicillin production in Penicillium chrysogenum
Biotechnol. Bioeng.
106
608-618
2010
Penicillium chrysogenum
Manually annotated by BRENDA team
Francis, W.R.; Shaner, N.C.; Christianson, L.M.; Powers, M.L.; Haddock, S.H.
Occurrence of isopenicillin-N-synthase homologs in bioluminescent ctenophores and implications for coelenterazine biosynthesis
PLoS ONE
10
e0128742
2015
Acremonium chrysogenum (P05189), Amycolatopsis lactamdurans (P27744), Aspergillus nidulans (P05326), Aspergillus nidulans ATCC 38163 (P05326), Crassostrea gigas (K1QF46), Flavobacterium sp. SC 12154 (P16020), Gordonia rubripertincta, Gordonia rubripertincta NBRC 101908, Lysobacter lactamgenus (Q48739), Mycolicibacterium phlei, Mycolicibacterium phlei RIVM601174, Penicillium chrysogenum (P08703), Streptomyces cattleya (Q53932), Streptomyces clavuligerus (P10621), Streptomyces clavuligerus ATCC 27064 (P10621), Streptomyces griseus (Q54243), Streptomyces jumonjinensis (P18286), Streptomyces microflavus (P12438)
Manually annotated by BRENDA team
Kurzatkowski, W.; Staniszewska, M.; Bondaryk, M.; Gebska-Kuczerowska, A.
Compartmentalization in penicillin G biosynthesis by Penicillium chrysogenum PQ-96
Pol. J. Microbiol.
63
399-408
2014
Penicillium chrysogenum, Penicillium chrysogenum PQ-96
Manually annotated by BRENDA team