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Literature summary extracted from

  • Castro, J.M.; Liras, P.; Laiz, L.; Cortes, J.; Martin, J.F.
    Purification and characterization of the isopenicillin N synthase of Streptomyces lactamdurans (1988), J. Gen. Microbiol., 134, 133-141.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.21.3.1 ascorbic acid required Penicillium chrysogenum
1.21.3.1 ascorbic acid required Acremonium chrysogenum
1.21.3.1 ascorbic acid great stimulation Amycolatopsis lactamdurans
1.21.3.1 dithiothreitol required, stimulating Amycolatopsis lactamdurans
1.21.3.1 O2 required Penicillium chrysogenum
1.21.3.1 O2 required Amycolatopsis lactamdurans
1.21.3.1 O2 required Acremonium chrysogenum

Application

EC Number Application Comment Organism
1.21.3.1 synthesis direct enzymic synthesis of antibiotics Amycolatopsis lactamdurans

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.21.3.1 Co2+
-
 Amycolatopsis lactamdurans
1.21.3.1 Cu2+ slight inhibition Amycolatopsis lactamdurans
1.21.3.1 D-glucose 6-phosphate strong inhibition Amycolatopsis lactamdurans
1.21.3.1 glutathione slight inhibition Amycolatopsis lactamdurans
1.21.3.1 Mn2+ moderate inhibition Amycolatopsis lactamdurans
1.21.3.1 additional information
-
 Acremonium chrysogenum
1.21.3.1 additional information anions F-, I-, Br-, Cl-, NO3-, H2PO4-, (AsO3)3-, (SO4)2- do not affect the activity; cations Na+, K+, Mg2+, Ca2+, Fe3+ do not affect the activity Amycolatopsis lactamdurans
1.21.3.1 additional information
-
 Penicillium chrysogenum
1.21.3.1 NH4+ inhibition of enzyme formation in vivo, no inhibitory effect in vitro Amycolatopsis lactamdurans
1.21.3.1 pyruvate slight inhibition Amycolatopsis lactamdurans
1.21.3.1 Zn2+ moderate inhibition Amycolatopsis lactamdurans

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.21.3.1 0.18
-
 delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine
-
 Amycolatopsis lactamdurans

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
1.21.3.1 cytosol
-
 Amycolatopsis lactamdurans 5829
-
1.21.3.1 cytosol
-
 Acremonium chrysogenum 5829
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.21.3.1 Fe2+ required Penicillium chrysogenum
1.21.3.1 Fe2+ required Amycolatopsis lactamdurans
1.21.3.1 Fe2+ required Acremonium chrysogenum

Molecular Weight [Da]

EC Number Molecular Weight [Da] Molecular Weight Maximum [Da] Comment Organism
1.21.3.1 26500
-
 gel filtration Amycolatopsis lactamdurans

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 Penicillium chrysogenum common step in the biosynthesis of penicillins, cephalosporins and cephamycins isopenicillin N + 2 H2O product has antibiotic activity ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 Amycolatopsis lactamdurans common step in the biosynthesis of penicillins, cephalosporins and cephamycins isopenicillin N + 2 H2O product has antibiotic activity ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 Acremonium chrysogenum common step in the biosynthesis of penicillins, cephalosporins and cephamycins isopenicillin N + 2 H2O product has antibiotic activity ?

Organism

EC Number Organism UniProt Comment Textmining
1.21.3.1 Acremonium chrysogenum
-
 i.e. Acremonium chrysogenum
-
1.21.3.1 Amycolatopsis lactamdurans
-
 i.e. Nocardia lactamdurans, NRRL 3802 var. JC 1843, cephamycin producing strain, Amy+ mutant
-
1.21.3.1 Penicillium chrysogenum
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.21.3.1
-
 Amycolatopsis lactamdurans

Reaction

EC Number Reaction Comment Organism Reaction ID
1.21.3.1 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 Penicillium chrysogenum
a
1.21.3.1 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 Amycolatopsis lactamdurans
a
1.21.3.1 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 Acremonium chrysogenum
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.21.3.1 mycelium
-
 Amycolatopsis lactamdurans
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.21.3.1 delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine + O2
-
 Amycolatopsis lactamdurans isopenicillin N + H2O
-
 r
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
-
 Penicillium chrysogenum isopenicillin N + 2 H2O
-
 ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
-
 Amycolatopsis lactamdurans isopenicillin N + 2 H2O
-
 ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
-
 Acremonium chrysogenum isopenicillin N + 2 H2O
-
 ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 common step in the biosynthesis of penicillins, cephalosporins and cephamycins Penicillium chrysogenum isopenicillin N + 2 H2O product has antibiotic activity ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 common step in the biosynthesis of penicillins, cephalosporins and cephamycins Amycolatopsis lactamdurans isopenicillin N + 2 H2O product has antibiotic activity ?
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 common step in the biosynthesis of penicillins, cephalosporins and cephamycins Acremonium chrysogenum isopenicillin N + 2 H2O product has antibiotic activity ?

Subunits

EC Number Subunits Comment Organism
1.21.3.1 monomer 1 * 26500, SDS-PAGE Amycolatopsis lactamdurans

Synonyms

EC Number Synonyms Comment Organism
1.21.3.1 IPN synthase ATP is not required, and therefore the enzyme should be named IPN synthase rather than IPN synthetase Amycolatopsis lactamdurans
1.21.3.1 IPNS
-
 Penicillium chrysogenum
1.21.3.1 IPNS
-
 Amycolatopsis lactamdurans
1.21.3.1 IPNS
-
 Acremonium chrysogenum
1.21.3.1 isopenicillin N synthase (cyclase)
-
 Penicillium chrysogenum
1.21.3.1 isopenicillin N synthase (cyclase)
-
 Acremonium chrysogenum
1.21.3.1 isopenicillin N synthase (cyclase) ATP is not required, and therefore the enzyme should be named IPN synthase rather than IPN synthetase Amycolatopsis lactamdurans

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.21.3.1 25
-
-
 Amycolatopsis lactamdurans

Temperature Range [°C]

EC Number Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
1.21.3.1 15 35
-
 Amycolatopsis lactamdurans

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.21.3.1 7
-
 pI 6.55 Amycolatopsis lactamdurans

pH Range

EC Number pH Minimum pH Maximum Comment Organism
1.21.3.1 5.8 9
-
 Amycolatopsis lactamdurans