Reference on EC 1.21.3.1 - isopenicillin-N synthase
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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
Rollins, M.J.; Jensen, S.E.; Westlake, D.W.S.
Isopenicillin N synthase and desacetoxycephalosporin C synthase activities during defined medium fermentations of Streptomyces clavuligerus: effect of oxygen and iron supplements
Can. J. Microbiol.
35
1111-1117
1989
Streptomyces clavuligerus
Palissa, H.; Von Doehren, H.; Kleinkauf, H.; Ting, H.H.; Baldwin, J.E.
beta-Lactam biosynthesis in a Gram-negative eubacterium: purification and characterization of isopenicillin N synthase from Flavobacterium sp. strain SC 12.154
J. Bacteriol.
171
5720-5728
1989
Flavobacterium sp., Flavobacterium sp. SC 12.154
Kriauciunas, A.; Frolik, C.A.; Hassell, T.C.; Skatrud, P.L.; Johnson, M.G.; Holbrook, N.L.; Chen, V.J.
The functional role of cysteines in isopenicillin N synthase. Correlation of cysteine reactivities toward sulfhydryl reagents with kinetic properties of cysteine mutants
J. Biol. Chem.
266
11779-11788
1991
Acremonium chrysogenum
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
Tan, D.S.H.; Sim, T.S.
Functional analysis of conserved histidine residues in Cephalosporium acremonium isopenicillin N synthase by site-directed mutagenesis
J. Biol. Chem.
271
889-894
1996
Acremonium chrysogenum
Roach, P.L.; Clifton, I.J.; Fulop, V.; Harlos, K.; Barton, G.J.; Hajdu, J.; Andersson, I.; Schofield, C.J.; Baldwin, J.E.
Crystal structure of isopenicillin N synthase is the first from a new structural family of enzymes
Nature
375
700-704
1995
Aspergillus nidulans (P05326)
Durairaj, M.; Leskiw, B.K.; Jensen, S.E.
Genetic and biochemical analysis of the cysteinyl residues of isopenicillin N synthase from Streptomyces clavuligerus
Can. J. Microbiol.
42
870-875
1996
Streptomyces clavuligerus
Roach, P.L.; Clifton, I.J.; Hensgens, C.M.H.; Shibta, N.; Schofield, C.J.; Hajdu, J.; Baldwin, J.E.
Structure of isopenicillin N synthase complexed with substrate and the mechanism of penicillin formation
Nature
387
827-830
1997
Aspergillus nidulans (P05326)
Kreisberg-Zakarin, R.; Borovok, I.; Yanko, M.; Aharonowitz, Y.; Cohen, G.
Recent advances in the structure and function of isopenicillin N synthase
Antonie van Leeuwenhoek
75
33-39
1999
Acremonium chrysogenum, Aspergillus nidulans, Aspergillus nidulans (P05326), Streptomyces jumonjinensis
Loke, P.; Sim, T.S.
Analysis of glutamines in catalysis in Cephalosporium acremonium isopenicillin N synthase by site-directed mutagenesis
Biochem. Biophys. Res. Commun.
252
472-475
1998
Acremonium chrysogenum
Rowe, C.J.; Shorrock, C.P.; Claridge, T.D.W.; Sutherland, J.D.
Analysis of the conversion of d-(L-alpha-aminoadipoyl)-L-cysteinyl-D-a-aminobutyrate by active-site mutants of Aspergillus nidulans isopenicillin N synthase
Chem. Biol.
5
229-239
1998
Aspergillus nidulans
Loke, P.; Ng, C.P.; Sim, T.S.
PCR cloning, heterologous expression, and characterization of isopenicillin N synthase from Streptomyces lipmanii NRRL 3584
Can. J. Microbiol.
46
166-170
2000
Streptomyces microflavus, Streptomyces microflavus NRRL 3584
Dubus, A.; Sami, M.; Brown, T.J.N.; Schofield, C.J.; Baldwin, J.E.; Frere, J.M.
Studies of isopenicillin N synthase enzymatic properties using a continuous spectrophotometric assay
FEBS Lett.
485
142-146
2000
Aspergillus nidulans
Kreisberg-Zakarin, R.; Borovok, I.; Yanko, M.; Frolow, F.; Aharonowitz, Y.; Cohen, G.
Structure-function studies of the non-heme iron active site of isopenicillin N synthase: some implications for catalysis
Biophys. Chem.
86
109-118
2000
Streptomyces jumonjinensis
Loke, P.; Sim, T.S.
Site-directed mutagenesis of proline-285 to leucine in Cephalosporium acremonium isopenicillin N-synthase affects catalysis and increases soluble expression at higher temperatures
Z. Naturforsch. C
56
413-415
2001
Acremonium chrysogenum
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
Ullan, R.V.; Casqueiro, J.; Banuelos, O.; Fernandez, F.J.; Gutierrez, S.; Martin, J.F.
A novel epimerization system in fungal secondary metabolism involved in the conversion of isopenicillin N into penicillin N in Acremonium chrysogenum
J. Biol. Chem.
277
46216-46225
2002
Acremonium chrysogenum, Acremonium chrysogenum C10 / ATCC 48272
Long, A.J.; Clifton, I.J.; Roach, P.L.; Baldwin, J.E.; Rutledge, P.J.; Schofield, C.J.
Structural studies on the reaction of isopenicillin N synthase with the truncated substrate analogues delta-(L-alpha-aminoadipoyl)-L-cysteinyl-glycine and delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-alanine
Biochemistry
44
6619-6628
2005
Aspergillus nidulans (P05326)
Howard-Jones, A.R.; Elkins, J.M.; Clifton, I.J.; Roach, P.L.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
Interactions of isopenicillin N synthase with cyclopropyl-containing substrate analogues reveal new mechanistic insight
Biochemistry
46
4755-4762
2007
Aspergillus nidulans (P05326)
Daruzzaman, A.; Clifton, I.J.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
Unexpected oxidation of a depsipeptide substrate analogue in crystalline isopenicillin N synthase
Chembiochem
7
351-358
2006
Aspergillus nidulans (P05326)
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
Brown, C.D.; Neidig, M.L.; Neibergall, M.B.; Lipscomb, J.D.; Solomon, E.I.
VTVH-MCD and DFT studies of thiolate bonding to [FeNO]7/[FeO2]8 complexes of isopenicillin N synthase: substrate determination of oxidase versus oxygenase activity in non-heme Fe enzymes
J. Am. Chem. Soc.
129
7427-7438
2007
Streptomyces microflavus
Lundberg, M.; Siegbahn, P.E.; Morokuma, K.
The mechanism for isopenicillin N synthase from density-functional modeling highlights the similarities with other enzymes in the 2-His-1-carboxylate family
Biochemistry
47
1031-1042
2008
Aspergillus nidulans
Ge, W.; Clifton, I.J.; Howard-Jones, A.R.; Stok, J.E.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
Structural studies on the reaction of isopenicillin N synthase with a sterically demanding depsipeptide substrate analogue
ChemBioChem
10
2025-2031
2009
Aspergillus nidulans (P05326)
Ge, W.; Clifton, I.J.; Stok, J.E.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
Isopenicillin N synthase mediates thiolate oxidation to sulfenate in a depsipeptide substrate analogue: implications for oxygen binding and a link to nitrile hydratase?
J. Am. Chem. Soc.
130
10096-10102
2008
Aspergillus nidulans
Liras, P.; Demain, A.L.
Enzymology of beta-lactam compounds with cephem structure produced by actinomycete
Methods Enzymol.
458
401-429
2009
Actinomyces sp.
Brown-Marshall, C.D.; Diebold, A.R.; Solomon, E.I.
Reaction coordinate of isopenicillin N synthase: oxidase versus oxygenase activity
Biochemistry
49
1176-1182
2010
Aspergillus nidulans
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
Clifton, I.J.; Ge, W.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
The crystal structure of isopenicillin N synthase with delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-methionine reveals thioether coordination to iron
Arch. Biochem. Biophys.
516
103-107
2011
Aspergillus nidulans (P05326), Aspergillus nidulans ATCC 38163 (P05326)
Daruzzaman, A.; Clifton, I.J.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
The interaction of isopenicillin N synthase with homologated substrate analogues delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-Xaa characterised by protein crystallography
ChemBioChem
14
599-606
2013
Aspergillus nidulans (P05326), Aspergillus nidulans ATCC 38163 (P05326)
Clifton, I.J.; Ge, W.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.
The crystal structure of an isopenicillin N synthase complex with an ethereal substrate analogue reveals water in the oxygen binding site
FEBS Lett.
587
2705-2709
2013
Aspergillus nidulans (P05326), Aspergillus nidulans ATCC 38163 (P05326)
Roelofs, D.; Timmermans, M.J.; Hensbergen, P.; van Leeuwen, H.; Koopman, J.; Faddeeva, A.; Suring, W.; de Boer, T.E.; Marien, J.; Boer, R.; Bovenberg, R.; van Straalen, N.M.
A functional isopenicillin N synthase in an animal genome
Mol. Biol. Evol.
30
541-548
2013
Folsomia candida (K9MVH8), Folsomia candida
McNeill, L.A.; Brown, T.J.N.; Sami, M.; Clifton, I.J.; Burzlaff, N.I.; Claridge, T.D.W.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.; Schofield, C.J.
Terminally truncated isopenicillin N synthase generates a dithioester product evidence for a thioaldehyde intermediate during catalysis and a new mode of reaction for non-heme iron oxidases
Chemistry
23
12815-12824
2017
Aspergillus nidulans (P05326), Aspergillus nidulans ATCC 38163 (P05326)
Wang, H.; Pan, Y.; Hu, P.; Zhu, Y.; Li, J.; Jiang, X.; Liu, G.
The autophagy-related gene Acatg1 is involved in conidiation and cephalosporin production in Acremonium chrysogenum
Fungal Genet. Biol.
69
65-74
2014
Acremonium chrysogenum, Acremonium chrysogenum 3.3795
Tamanaha, E.; Zhang, B.; Guo, Y.; Chang, W.C.; Barr, E.W.; Xing, G.; St Clair, J.; Ye, S.; Neese, F.; Bollinger, J.M.; Krebs, C.
Spectroscopic evidence for the Two C-H-cleaving intermediates of Aspergillus nidulans isopenicillin N synthase
J. Am. Chem. Soc.
138
8862-8874
2016
Aspergillus nidulans
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
Mycolicibacterium phlei, Gordonia rubripertincta, Crassostrea gigas (K1QF46), Acremonium chrysogenum (P05189), Aspergillus nidulans (P05326), Penicillium chrysogenum (P08703), Streptomyces clavuligerus (P10621), Streptomyces microflavus (P12438), Flavobacterium sp. SC 12154 (P16020), Streptomyces jumonjinensis (P18286), Amycolatopsis lactamdurans (P27744), Lysobacter lactamgenus (Q48739), Streptomyces cattleya (Q53932), Streptomyces griseus (Q54243), Mycolicibacterium phlei RIVM601174, Aspergillus nidulans ATCC 38163 (P05326), Streptomyces clavuligerus ATCC 27064 (P10621), Gordonia rubripertincta NBRC 101908
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