1.21.3.1 adipyl-L-cysteinyl-D-valine + ? - Actinomyces sp. N-(4-carboxybutyl)penicillin + 2 H2O - ? 402405 1.21.3.1 delta-(L-alpha-aminoadipoyl)-(3R)-methyl-L-cysteine D-alpha hydroxyvaleryl ester + O2 - Aspergillus nidulans ? + H2O - ? 388515 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteine D-alpha-hydroxyisovaleryl ester + O2 - Aspergillus nidulans (2S)-2-amino-6-([(2R)-1-[(1S)-1-carboxy-2-methylpropoxy]-1,3-dioxo-3-sulfanylpropan-2-yl]amino)-6-oxohexanoic acid + H2O - ? 443454 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteine D-alpha-hydroxyisovaleryl ester + O2 - Aspergillus nidulans ATCC 38163 (2S)-2-amino-6-([(2R)-1-[(1S)-1-carboxy-2-methylpropoxy]-1,3-dioxo-3-sulfanylpropan-2-yl]amino)-6-oxohexanoic acid + H2O - ? 443454 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteine D-alpha-hydroxyisovaleryl ester + O2 - Aspergillus nidulans ? - ? 443455 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteine D-alpha-hydroxyisovaleryl ester + O2 - Aspergillus nidulans ATCC 38163 ? - ? 443455 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteinyl-beta-methyl-D-cyclopropylglycine + O2 - Aspergillus nidulans (2R,8R)-8-([(5S)-5-amino-5-carboxypentanoyl]amino)-3-methylene-9-oxo-6-thia-1-azabicyclo[5.2.0]nonane-2-carboxylic acid + H2O - ? 388516 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-alpha-hydroxyisovaleryl ester + O2 for this substrate analogue (ACOV) lacking an amide nitrogen IPNS exhibits oxygenase activity Aspergillus nidulans ? - ? 416871 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteinyl-O-methyl-D-allo-threonine + O2 - Aspergillus nidulans (2S,3S,5R,6R)-6-[[(5S)-5-amino-5-carboxypentanoyl]amino]-3-methoxy-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid + 2 H2O product is a bioactive penam. Epimeric delta-(L-alpha-aminoadipoyl)-L-cysteinyl-O-methyl-D-threonine is not turned over by the enzyme ? 428562 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-cysteinyl-O-methyl-D-allo-threonine + O2 - Aspergillus nidulans ATCC 38163 (2S,3S,5R,6R)-6-[[(5S)-5-amino-5-carboxypentanoyl]amino]-3-methoxy-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid + 2 H2O product is a bioactive penam. Epimeric delta-(L-alpha-aminoadipoyl)-L-cysteinyl-O-methyl-D-threonine is not turned over by the enzyme ? 428562 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-cysteine + O2 - Aspergillus nidulans (4S,7S)-7-[[(5S)-5-amino-5-carboxypentanoyl]amino]-6-oxohexahydropyrrolo[2,1-c][1,2,4]dithiazine-4-carboxylic acid + 2 H2O product is a bicyclic gamma-lactam disulfide ? 428563 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-cysteine + O2 - Aspergillus nidulans ATCC 38163 (4S,7S)-7-[[(5S)-5-amino-5-carboxypentanoyl]amino]-6-oxohexahydropyrrolo[2,1-c][1,2,4]dithiazine-4-carboxylic acid + 2 H2O product is a bicyclic gamma-lactam disulfide ? 428563 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine + O2 - Aspergillus nidulans (2S)-2-amino-6-([(3S)-1-[(1R)-1-carboxy-2-methylpropyl]-5-hydroxy-2-oxopyrrolidin-3-yl]mino)-6-oxohexanoic acid + ? enzyme converts the homologated tripeptides delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine and delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-allylglycine into monocyclic hydroxy-lactam products, suggesting that the additional methylene unit in these substrates induces conformational changes that preclude second ring closure after initial lactam formation ? 428564 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine + O2 - Aspergillus nidulans ATCC 38163 (2S)-2-amino-6-([(3S)-1-[(1R)-1-carboxy-2-methylpropyl]-5-hydroxy-2-oxopyrrolidin-3-yl]mino)-6-oxohexanoic acid + ? enzyme converts the homologated tripeptides delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine and delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-allylglycine into monocyclic hydroxy-lactam products, suggesting that the additional methylene unit in these substrates induces conformational changes that preclude second ring closure after initial lactam formation ? 428564 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-delta-S-methylcysteine + O2 - Aspergillus nidulans ? enzyme converts the homologated tripeptides delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine and delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-allylglycine into monocyclic hydroxy-lactam products, suggesting that the additional methylene unit in these substrates induces conformational changes that preclude second ring closure after initial lactam formation ? 428565 1.21.3.1 delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-delta-S-methylcysteine + O2 - Aspergillus nidulans ATCC 38163 ? enzyme converts the homologated tripeptides delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine and delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-allylglycine into monocyclic hydroxy-lactam products, suggesting that the additional methylene unit in these substrates induces conformational changes that preclude second ring closure after initial lactam formation ? 428565 1.21.3.1 delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-alpha-aminobutyrate + O2 wild-type and mutants, reaction mechanism Aspergillus nidulans ? - ir 289314 1.21.3.1 delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine + O2 - Flavobacterium sp. isopenicillin N + H2O - r 451483 1.21.3.1 delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine + O2 - Amycolatopsis lactamdurans isopenicillin N + H2O - r 451483 1.21.3.1 delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine + O2 - Flavobacterium sp. SC 12.154 isopenicillin N + H2O - r 451483 1.21.3.1 delta-L-alpha-aminoadipoyl-L-cysteine (1-(S)-carboxy-2-thiomethyl)ethyl ester + O2 substrate analogue Aspergillus nidulans ? + H2O - ? 405551 1.21.3.1 delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 - Aspergillus nidulans isopenicillin N + 2 H2O - ? 402650 1.21.3.1 delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 for the native substrate IPNS shows oxidase activity Aspergillus nidulans isopenicillin N + 2 H2O - ? 402650 1.21.3.1 delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 - Folsomia candida ? - ? 428566 1.21.3.1 L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 - Aspergillus nidulans ? + H2O - ? 402721 1.21.3.1 L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 - Aspergillus nidulans isopenicillin N + 2 H2O - ? 402722 1.21.3.1 L-delta-(alpha-aminoadipoyl)-L-cysteinyl-glycine + O2 - Aspergillus nidulans (2S)-2-amino-6-([(2S)-1-[(carboxymethyl)amino]-3,3-dihydroxy-1-oxopropan-2-yl]amino)-6-oxohexanoic acid + H2O - ? 443675 1.21.3.1 L-delta-(alpha-aminoadipoyl)-L-cysteinyl-glycine + O2 - Aspergillus nidulans ATCC 38163 (2S)-2-amino-6-([(2S)-1-[(carboxymethyl)amino]-3,3-dihydroxy-1-oxopropan-2-yl]amino)-6-oxohexanoic acid + H2O - ? 443675 1.21.3.1 L-delta-(alpha-aminoadipoyl)-L-cysteinyl-glycine + O2 - Aspergillus nidulans ? - ? 443676 1.21.3.1 L-delta-(alpha-aminoadipoyl)-L-cysteinyl-glycine + O2 - Aspergillus nidulans ATCC 38163 ? - ? 443676 1.21.3.1 additional information delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-alpha-aminobutyrate as substrate is converted to 3 different products: an alpha- and a beta-methyl-penam, and a cepham Aspergillus nidulans ? - ? 89 1.21.3.1 additional information in Penicillium chrysogenum, the enzymes involved in penicillin production are compartmentalized in the cytosol and in microbodies Penicillium chrysogenum ? - ? 89 1.21.3.1 additional information iron-mediated conversion of metal-bound thiolate to sulfenate in crystallographic studies Aspergillus nidulans ? - ? 89 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Aspergillus nidulans isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Penicillium chrysogenum isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Flavobacterium sp. isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Amycolatopsis lactamdurans isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces microflavus isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Acremonium chrysogenum isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces clavuligerus isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces jumonjinensis isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 catalytic reaction is under steric regulation Aspergillus nidulans isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 catalytic reaction is under steric regulation Aspergillus nidulans isopenicillin N + 2 H2O product has antibiotic activity ? 289313 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 Aspergillus nidulans isopenicillin N + 2 H2O - ? 289313 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 - ? 289313 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 Streptomyces microflavus isopenicillin N + 2 H2O - ? 289313 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 - ? 289313 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 Aspergillus nidulans isopenicillin N + 2 H2O product has antibiotic activity ? 289313 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 ? 289313 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 Flavobacterium sp. isopenicillin N + 2 H2O product has antibiotic activity ? 289313 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 ? 289313 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 ? 289313 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 Streptomyces clavuligerus isopenicillin N + 2 H2O product has antibiotic activity ? 289313 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 Streptomyces jumonjinensis isopenicillin N + 2 H2O product has antibiotic activity ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 modifications of the L-cysteine residue in the second position of the enzyme result in tripeptides that are unable to serve as substrates Penicillium chrysogenum isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 modifications of the L-cysteine residue in the second position of the enzyme result in tripeptides that are unable to serve as substrates Acremonium chrysogenum isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 evaluation of culture conditions for penicillin and cephalosporin C production Streptomyces clavuligerus isopenicillin N + 2 H2O product has antibiotic activity ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 key enzyme of the biosynthetic pathway Aspergillus nidulans isopenicillin N + 2 H2O product has antibiotic activity ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 key enzyme of the biosynthetic pathway Acremonium chrysogenum isopenicillin N + 2 H2O product has antibiotic activity ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 key enzyme of the biosynthetic pathway Streptomyces jumonjinensis isopenicillin N + 2 H2O product has antibiotic activity ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 involved in biosynthesis of cephalosporin C Acremonium chrysogenum isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 IPNSs are nonheme iron-dependent oxygenases that catalyze cyclization Actinomyces sp. isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Flavobacterium sp. SC 12.154 isopenicillin N + 2 H2O - ? 289313 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 Flavobacterium sp. SC 12.154 isopenicillin N + 2 H2O product has antibiotic activity ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces microflavus NRRL 3584 isopenicillin N + 2 H2O - ? 289313 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 Streptomyces microflavus NRRL 3584 isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Acremonium chrysogenum C10 / ATCC 48272 isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 involved in biosynthesis of cephalosporin C Acremonium chrysogenum C10 / ATCC 48272 isopenicillin N + 2 H2O - ? 289313 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces microflavus isopenicillin + H2O - ? 394923 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 the enzyme catalyzes the four electron oxidative double ring closure of its substrate Streptomyces microflavus isopenicillin + H2O - ? 394923 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Aspergillus nidulans isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Penicillium chrysogenum isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Mycolicibacterium phlei isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Gordonia rubripertincta isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Acremonium chrysogenum isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces microflavus isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces cattleya isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Amycolatopsis lactamdurans isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Crassostrea gigas isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces clavuligerus isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Lysobacter lactamgenus isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Flavobacterium sp. SC 12154 isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces griseus isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces jumonjinensis isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Mycolicibacterium phlei RIVM601174 isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Aspergillus nidulans ATCC 38163 isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Streptomyces clavuligerus ATCC 27064 isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Penicillium chrysogenum PQ-96 isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Acremonium chrysogenum 3.3795 isopenicillin N + H2O - ? 442483 1.21.3.1 N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 - Gordonia rubripertincta NBRC 101908 isopenicillin N + H2O - ? 442483 1.21.3.1 N6-[(1R,2S)-1-([[(1R)-1-carboxy-2-methylpropyl]oxy]carbonyl)-2-sulfanylpropyl]-6-oxo-L-lysine + O2 substrate analogue Aspergillus nidulans ? + H2O - ? 406066 1.21.3.1 phenylacetyl-L-cysteinyl-D-valine + O2 - Actinomyces sp. penicillin G + 2 H2O - ? 402520