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1.21.3.1: isopenicillin-N synthase

This is an abbreviated version!
For detailed information about isopenicillin-N synthase, go to the full flat file.

Word Map on EC 1.21.3.1

Reaction

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

Synonyms

IPN cyclase, IPN synthase, IPNS, isopenicillin N synthase, isopenicillin N synthase (cyclase), isopenicillin N synthetase, isopenicillin N-synthase, isopenicillin-N synthase, isopenicillin-N-synthase, More, PcbC, synthetase, isopenicillin N (9Cl)

ECTree

     1 Oxidoreductases
         1.21 Catalysing the reaction X-H + Y-H = X-Y
             1.21.3 With oxygen as acceptor
                1.21.3.1 isopenicillin-N synthase

Substrates Products

Substrates Products on EC 1.21.3.1 - isopenicillin-N synthase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
adipyl-L-cysteinyl-D-valine + ?
N-(4-carboxybutyl)penicillin + 2 H2O
show the reaction diagram
-
-
-
-
?
delta-(L-alpha-aminoadipoyl)-(3R)-methyl-L-cysteine D-alpha hydroxyvaleryl ester + O2
? + H2O
show the reaction diagram
-
-
-
?
delta-(L-alpha-aminoadipoyl)-L-cysteine D-alpha-hydroxyisovaleryl ester + O2
(2S)-2-amino-6-([(2R)-1-[(1S)-1-carboxy-2-methylpropoxy]-1,3-dioxo-3-sulfanylpropan-2-yl]amino)-6-oxohexanoic acid + H2O
show the reaction diagram
delta-(L-alpha-aminoadipoyl)-L-cysteine D-alpha-hydroxyisovaleryl ester + O2
?
show the reaction diagram
delta-(L-alpha-aminoadipoyl)-L-cysteinyl-beta-methyl-D-cyclopropylglycine + O2
(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
show the reaction diagram
-
-
-
?
delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-alpha-hydroxyisovaleryl ester + O2
?
show the reaction diagram
-
for this substrate analogue (ACOV) lacking an amide nitrogen IPNS exhibits oxygenase activity
-
-
?
delta-(L-alpha-aminoadipoyl)-L-cysteinyl-O-methyl-D-allo-threonine + O2
(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
show the reaction diagram
delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-cysteine + O2
(4S,7S)-7-[[(5S)-5-amino-5-carboxypentanoyl]amino]-6-oxohexahydropyrrolo[2,1-c][1,2,4]dithiazine-4-carboxylic acid + 2 H2O
show the reaction diagram
delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-D-valine + O2
(2S)-2-amino-6-([(3S)-1-[(1R)-1-carboxy-2-methylpropyl]-5-hydroxy-2-oxopyrrolidin-3-yl]mino)-6-oxohexanoic acid + ?
show the reaction diagram
delta-(L-alpha-aminoadipoyl)-L-homocysteinyl-delta-S-methylcysteine + O2
?
show the reaction diagram
delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-alpha-aminobutyrate + O2
?
show the reaction diagram
-
wild-type and mutants, reaction mechanism
-
-
ir
delta-(L-alpha-aminoadipyl)-L-cysteinyl-D-valine + O2
isopenicillin N + H2O
show the reaction diagram
delta-L-alpha-aminoadipoyl-L-cysteine (1-(S)-carboxy-2-thiomethyl)ethyl ester + O2
? + H2O
show the reaction diagram
-
substrate analogue
-
-
?
delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2
?
show the reaction diagram
-
-
-
?
delta-L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2
isopenicillin N + 2 H2O
show the reaction diagram
L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2
? + H2O
show the reaction diagram
-
-
-
-
?
L-alpha-aminoadipoyl-L-cysteinyl-D-valine + O2
isopenicillin N + 2 H2O
show the reaction diagram
-
-
-
-
?
L-delta-(alpha-aminoadipoyl)-L-cysteinyl-glycine + O2
(2S)-2-amino-6-([(2S)-1-[(carboxymethyl)amino]-3,3-dihydroxy-1-oxopropan-2-yl]amino)-6-oxohexanoic acid + H2O
show the reaction diagram
L-delta-(alpha-aminoadipoyl)-L-cysteinyl-glycine + O2
?
show the reaction diagram
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin + H2O
show the reaction diagram
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + 2 H2O
show the reaction diagram
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine + O2
isopenicillin N + H2O
show the reaction diagram
N6-[(1R,2S)-1-([[(1R)-1-carboxy-2-methylpropyl]oxy]carbonyl)-2-sulfanylpropyl]-6-oxo-L-lysine + O2
? + H2O
show the reaction diagram
substrate analogue
-
-
?
phenylacetyl-L-cysteinyl-D-valine + O2
penicillin G + 2 H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-