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Roles as Enzyme Ligand
Enzyme Kinetic Parameters
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Ligand N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine

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Basic Ligand Information

Molecular Structure

Picture of N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine (click for magnification)

Molecular Formula

BRENDA Name

InChIKey

C₁₄H₂₅N₃O₆S

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine

BYEIJZFKOAXBBV-ATZCPNFKSA-N

Synonyms:

delta(L-2-aminoadipyl)-L-cysteinyl-D-valine, delta-(L-2-aminoadipyl)-L-cysteinyl-D-valine, delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine, L-alpha-aminoadipoyl-L-cysteinyl-D-valine, L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine, N-[L-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine

Pathway Source

Pathways

KEGG

Biosynthesis of secondary metabolites, Penicillin and cephalosporin biosynthesis

MetaCyc

isopenicillin N biosynthesis

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (96 results)

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Show Natural Substrate (96 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

2bjs, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6y0o, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zae, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zaf, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zag, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zah, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zai, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zaj, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zak, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zal, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zam, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zan, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zap, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

6zw8, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

7poy, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317

7psw, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

2bjs, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6y0o, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zae, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zaf, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zag, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zah, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zai, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zaj, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zak, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zal, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zam, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zan, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zap, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zw8, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

7poy, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

7psw, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

2bjs, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6y0o, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zae, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zaf, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zag, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zah, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zai, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zaj, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zak, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zal, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zam, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zan, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zap, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zw8, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

7poy, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

7psw, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

2bjs, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6y0o, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zae, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zaf, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zag, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zah, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zai, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zaj, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zak, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zal, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zam, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zan, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zap, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zw8, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

7poy, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

7psw, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

2bjs, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6y0o, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zae, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zaf, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zag, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zah, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zai, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zaj, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zak, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zal, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zam, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zan, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zap, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

6zw8, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

7poy, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440330, 440328, 440325, 440327, 440318, 440326, 440317, 440319, 440324, 440329, 440323, 440314, 440316, 440315, 440321, 440320, 440322, 492265, 700004

7psw, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

2bjs, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6y0o, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zae, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zaf, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zag, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zah, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zai, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zaj, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zak, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zal, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zam, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zan, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zap, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zw8, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

7poy, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

7psw, 3D-view

1.21.3.1

96 entries

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.26

alpha-aminoadipic acid + L-valine + L-lysine + ? = L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine + ?

6.3.2.26

3 ATP + L-2-aminohexanedioate + L-cysteine + L-valine + H2O = 3 AMP + 3 diphosphate + N-[L-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine

6.3.2.26

2 entries

Substrate in Enzyme-catalyzed Reactions (112 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

2bjs, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6y0o, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zae, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zaf, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zag, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zah, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zai, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zaj, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zak, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zal, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zam, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zan, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zap, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

6zw8, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

7poy, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ?

728275

7psw, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

2bjs, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6y0o, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zae, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zaf, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zag, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zah, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zai, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zaj, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zak, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zal, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zam, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zan, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zap, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

6zw8, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

7poy, 3D-view

1.21.3.1

delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

697317, 714183

7psw, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

2bjs, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6y0o, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zae, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zaf, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zag, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zah, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zai, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zaj, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zak, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zal, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zam, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zan, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zap, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

6zw8, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

7poy, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = ? + H2O

696215

7psw, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

2bjs, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6y0o, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zae, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zaf, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zag, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zah, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zai, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zaj, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zak, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zal, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zam, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zan, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zap, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

6zw8, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

7poy, 3D-view

1.21.3.1

L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

698457

7psw, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

2bjs, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6y0o, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zae, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zaf, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zag, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zah, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zai, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zaj, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zak, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zal, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zam, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zan, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zap, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

6zw8, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

7poy, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin + H2O

687292

7psw, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

2bjs, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6y0o, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zae, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zaf, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zag, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zah, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zai, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zaj, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zak, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zal, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zam, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zan, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zap, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

6zw8, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

7poy, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + 2 H2O

440323, 440327, 440314, 440318, 440330, 440316, 440326, 440317, 440319, 440324, 440329, 492265, 440315, 440321, 440320, 440322, 672246, 440328, 440325, 700004

7psw, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

2bjs, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6y0o, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zae, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zaf, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zag, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zah, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zai, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zaj, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zak, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zal, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zam, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zan, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zap, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

6zw8, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

7poy, 3D-view

1.21.3.1

N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2 = isopenicillin N + H2O

745172, 746275, 746185, 745018, 744719

7psw, 3D-view

1.21.3.1

112 entries

Product in Enzyme-catalyzed Reactions (2 results)

top print hide

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Product (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.26

alpha-aminoadipic acid + L-valine + L-lysine + ? = L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine + ?

6.3.2.26

3 ATP + L-2-aminohexanedioate + L-cysteine + L-valine + H2O = 3 AMP + 3 diphosphate + N-[L-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine

6.3.2.26

2 entries

Inhibitor in Enzyme-catalyzed Reactions (16 results)

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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

Show Inhibitors (16 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.21.3.1

substrate inhibition above 5 mM

440317

2bjs, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6y0o, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zae, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zaf, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zag, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zah, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zai, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zaj, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zak, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zal, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zam, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zan, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zap, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

6zw8, 3D-view

1.21.3.1

substrate inhibition above 5 mM

440317

7poy, 3D-view

1.21.3.1

substrate inhibition above 5 mM

3D Structure of Enzyme-Ligand-Complex (PDB) (112 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (112 entries)

EC NUMBER

ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (1 result)

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Show Turnover Number (1 entry)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.21.3.1

4.1

440327

K_M Value (3 results)

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Show KM Value (3 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.21.3.1

-999

Km values for ACV exhibit for different cyclases are on the order of 0.2-0.3 mM

0.12

0.18

References & Links

Literature References (31)

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Show Reference (31 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

440314

3183613

Purification and characterization of the isopenicillin N synthase of Streptomyces lactamdurans

1988

Castro, J.M.; Liras, P.; Laiz, L.; Cortes, J.; Martin, J.F.

J. Gen. Microbiol.

134

133-141

440315

2630033

Isopenicillin N synthase and desacetoxycephalosporin C synthase activities during defined medium fermentations of Streptomyces clavuligerus: effect of oxygen and iron supplements

1989

Rollins, M.J.; Jensen, S.E.; Westlake, D.W.S.

Can. J. Microbiol.

1111-1117

440316

2793834

beta-Lactam biosynthesis in a Gram-negative eubacterium: purification and characterization of isopenicillin N synthase from Flavobacterium sp. strain SC 12.154

1989

Palissa, H.; Von Doehren, H.; Kleinkauf, H.; Ting, H.H.; Baldwin, J.E.

J. Bacteriol.

171

5720-5728

440317

2050677

The functional role of cysteines in isopenicillin N synthase. Correlation of cysteine reactivities toward sulfhydryl reagents with kinetic properties of cysteine mutants

1991

Kriauciunas, A.; Frolik, C.A.; Hassell, T.C.; Skatrud, P.L.; Johnson, M.G.; Holbrook, N.L.; Chen, V.J.

J. Biol. Chem.

266

11779-11788

440318

1588566

Substrate specificity of isopenicillin N synthase

1992

Huffman, G.W.; Gesellchen, P.D.; Turner, J.R.; Rothenberger, R.B.; Osborne, H.E.; Miller, F.D.; Chapman, J.L.; Queener, S.W.

J. Med. Chem.

1897-1914

440319

8557701

Functional analysis of conserved histidine residues in Cephalosporium acremonium isopenicillin N synthase by site-directed mutagenesis

1996

Tan, D.S.H.; Sim, T.S.

J. Biol. Chem.

271

889-894

440320

7791906

Crystal structure of isopenicillin N synthase is the first from a new structural family of enzymes

1995

Roach, P.L.; Clifton, I.J.; Fulop, V.; Harlos, K.; Barton, G.J.; Hajdu, J.; Andersson, I.; Schofield, C.J.; Baldwin, J.E.

Nature

375

700-704

440321

8776857

Genetic and biochemical analysis of the cysteinyl residues of isopenicillin N synthase from Streptomyces clavuligerus

1996

Durairaj, M.; Leskiw, B.K.; Jensen, S.E.

Can. J. Microbiol.

870-875

440322

9194566

Structure of isopenicillin N synthase complexed with substrate and the mechanism of penicillin formation

1997

Roach, P.L.; Clifton, I.J.; Hensgens, C.M.H.; Shibta, N.; Schofield, C.J.; Hajdu, J.; Baldwin, J.E.

Nature

387

827-830

440323

10422580

Recent advances in the structure and function of isopenicillin N synthase

1999

Kreisberg-Zakarin, R.; Borovok, I.; Yanko, M.; Aharonowitz, Y.; Cohen, G.

Antonie van Leeuwenhoek

33-39

440324

9826554

Analysis of glutamines in catalysis in Cephalosporium acremonium isopenicillin N synthase by site-directed mutagenesis

1998

Loke, P.; Sim, T.S.

Biochem. Biophys. Res. Commun.

252

472-475

440325

9545433

Analysis of the conversion of d-(L-alpha-aminoadipoyl)-L-cysteinyl-D-a-aminobutyrate by active-site mutants of Aspergillus nidulans isopenicillin N synthase

1998

Rowe, C.J.; Shorrock, C.P.; Claridge, T.D.W.; Sutherland, J.D.

Chem. Biol.

229-239

440326

10721485

PCR cloning, heterologous expression, and characterization of isopenicillin N synthase from Streptomyces lipmanii NRRL 3584

2000

Loke, P.; Ng, C.P.; Sim, T.S.

Can. J. Microbiol.

166-170

440327

11094156

Studies of isopenicillin N synthase enzymatic properties using a continuous spectrophotometric assay

2000

Dubus, A.; Sami, M.; Brown, T.J.N.; Schofield, C.J.; Baldwin, J.E.; Frere, J.M.

FEBS Lett.

485

142-146

440328

11026676

Structure-function studies of the non-heme iron active site of isopenicillin N synthase: some implications for catalysis

2000

Kreisberg-Zakarin, R.; Borovok, I.; Yanko, M.; Frolow, F.; Aharonowitz, Y.; Cohen, G.

Biophys. Chem.

109-118

440329

11421458

Site-directed mutagenesis of proline-285 to leucine in Cephalosporium acremonium isopenicillin N-synthase affects catalysis and increases soluble expression at higher temperatures

2001

Loke, P.; Sim, T.S.

Z. Naturforsch. C

413-415

440330

3104145

Cloning and expression of the isopenicillin N synthetase from Penicillium chrysogenum

1986

Carr, L.G.; Skatrud, P.L.; Scheetz, M.E 2nd.; Queener, S.W.; Ingolia, T.D.

Gene

257-266

492265

12228250

A novel epimerization system in fungal secondary metabolism involved in the conversion of isopenicillin N into penicillin N in Acremonium chrysogenum

2002

Ullan, R.V.; Casqueiro, J.; Banuelos, O.; Fernandez, F.J.; Gutierrez, S.; Martin, J.F.

J. Biol. Chem.

277

46216-46225

672246

17397141

Interactions of isopenicillin N synthase with cyclopropyl-containing substrate analogues reveal new mechanistic insight

2007

Howard-Jones, A.R.; Elkins, J.M.; Clifton, I.J.; Roach, P.L.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.

Biochemistry

4755-4762

687292

17506560

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

2007

Brown, C.D.; Neidig, M.L.; Neibergall, M.B.; Lipscomb, J.D.; Solomon, E.I.

J. Am. Chem. Soc.

129

7427-7438

696215

18163649

The mechanism for isopenicillin N synthase from density-functional modeling highlights the similarities with other enzymes in the 2-His-1-carboxylate family

2008

Lundberg, M.; Siegbahn, P.E.; Morokuma, K.

Biochemistry

1031-1042

697317

19598184

Structural studies on the reaction of isopenicillin N synthase with a sterically demanding depsipeptide substrate analogue

2009

Ge, W.; Clifton, I.J.; Howard-Jones, A.R.; Stok, J.E.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.

ChemBioChem

2025-2031

698457

18620394

Isopenicillin N synthase mediates thiolate oxidation to sulfenate in a depsipeptide substrate analogue: implications for oxygen binding and a link to nitrile hydratase?

2008

Ge, W.; Clifton, I.J.; Stok, J.E.; Adlington, R.M.; Baldwin, J.E.; Rutledge, P.J.

J. Am. Chem. Soc.

130

10096-10102

700004

19374992

Enzymology of beta-lactam compounds with cephem structure produced by actinomycete

2009

Liras, P.; Demain, A.L.

Methods Enzymol.

458

401-429

714183

20078029

Reaction coordinate of isopenicillin N synthase: oxidase versus oxygenase activity

2010

Brown-Marshall, C.D.; Diebold, A.R.; Solomon, E.I.

Biochemistry

1176-1182

728275

23204388

A functional isopenicillin N synthase in an animal genome

2013

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.

Mol. Biol. Evol.

541-548

744719

28703303

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

2017

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.

Chemistry

12815-12824

745018

24963594

The autophagy-related gene Acatg1 is involved in conidiation and cephalosporin production in Acremonium chrysogenum

2014

Wang, H.; Pan, Y.; Hu, P.; Zhu, Y.; Li, J.; Jiang, X.; Liu, G.

Fungal Genet. Biol.

65-74

745172

27193226

Spectroscopic evidence for the Two C-H-cleaving intermediates of Aspergillus nidulans isopenicillin N synthase