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Literature summary extracted from

  • 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 (1991), J. Biol. Chem., 266, 11779-11788.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
1.21.3.1 O2 required Acremonium chrysogenum

Protein Variants

EC Number Protein Variants Comment Organism
1.21.3.1 C106S site-directed mutagenesis, 63% reduced activity, 14fold increased Km for N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine Acremonium chrysogenum
1.21.3.1 C106S/C255S site-directed mutagenesis, 63% reduced activity, 14fold increased Km for N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine Acremonium chrysogenum
1.21.3.1 C255S site-directed mutagenesis, 33% reduced activity, 1.4fold increased Km for N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine Acremonium chrysogenum

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.21.3.1 N-ethylmaleimide only Cys106 can be modified, partly blocked by substrate analogue inhibitors Acremonium chrysogenum
1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine substrate inhibition above 5 mM Acremonium chrysogenum

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 Acremonium chrysogenum common step in the biosynthesis of penicillins, cephalosporins and cephamycins isopenicillin N + 2 H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.21.3.1 Acremonium chrysogenum
-
 i.e. Acremonium chrysogenum
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.21.3.1 wild-type and mutants are purified as catalytically latent apoenzymes Acremonium chrysogenum

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 Cys106 is involved in substrate binding, Cys255 is involved in maintaining the protein structure Acremonium chrysogenum
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
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 Acremonium chrysogenum isopenicillin N + 2 H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.21.3.1 IPNS
-
 Acremonium chrysogenum

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
1.21.3.1 0.9
-
 N-ethylmaleimide about Acremonium chrysogenum