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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

Inhibitors

Inhibitors on EC 1.21.3.1 - isopenicillin-N synthase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
alpha-aminoadipic(-Cys-Gly)
bis[alpha-aminoadipic(-Cys-D-chloroalanine)]
bis[alpha-aminoadipic(-Cys-D-hexafluorovaline)]
bis[alpha-aminoadipic(-Cys-D-Phe)]
bis[alpha-aminoadipic(-Cys-D-Trp)]
bis[alpha-aminoadipic(-Cys-D-Tyr)]
bis[alpha-aminoadipic(-Cys-DL-hexafluorovaline)]
bis[alpha-aminoadipic(-Cys-hexafluorovaline)]
bis[H-Cys-D-Val]
Cu2+
-
slight inhibition
cystamine
-
100% inhibition at 0.5 mM
cysteamine
-
43% inhibition at 1.5 mM
cysteine
-
60% inhibition at 1 mM
cystine
-
81% inhibition at 1.5 mM
D-glucose 6-phosphate
-
strong inhibition
delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-cyclopropylglycine
-
delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-methionine
substrate analogue, which incorporates a thioether in place of the valinyl sidechain. Crystal structure of the enzyme in complex with the compound and Fe(II) at 1.40 A resolution reveals that the compound binds in the active site such that the sulfur atom of the methionine thioether binds to iron in the oxygen binding site at a distance of 2.57 A. The sulfur of the cysteinyl thiolate sits 2.36 A from the metal
delta-(L-alpha-aminoadipoyl)-L-cysteinyl-O-methyl-D-threonine
substrate analogue, not turned over by IPNS
glutathione
-
slight inhibition
GSH
-
70% inhibition at 1 mM
N-ethylmaleimide
N-[(5S)-5-amino-5-carboxypentanoyl]-L-cysteinyl-D-valine
-
substrate inhibition above 5 mM
NH4+
-
inhibition of enzyme formation in vivo, no inhibitory effect in vitro
Ni2+
-
moderate inhibition
pyruvate
-
slight inhibition
Triton X-100
-
inhibits at concentration of 0.5%
additional information
-