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Ligand dichlorochromopyrrolate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.17

dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ = 1,11-dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+

698452

-

1.13.12.17

dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ = dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+

698455, 698497, 700932

-

1.13.12.17

2 entries

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.98.2

7-chloroindole-3-pyruvic acid + 7-chlorotryptophan + O2 = 11,11'-dichlorochromopyrrolic acid + NH3 + H2O

0

-

1.21.98.2

4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2 = 2 dichlorochromopyrrolate + 2 NH3 + 2 H2O

0

-

1.21.98.2

2 3-(7-chloroindol-3-yl)-2-iminopropanoate + H2O2 = dichlorochromopyrrolate + NH3 + 2 H2O

0

-

1.21.98.2

3 entries

Substrate in Enzyme-catalyzed Reactions (2 results)

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Show Substrate (2 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.13.12.17

dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ = 1,11-dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+

698452

-

1.13.12.17

dichlorochromopyrrolate + 4 O2 + 4 NADH + 4 H+ = dichloroarcyriaflavin A + 2 CO2 + 6 H2O + 4 NAD+

698455, 700932, 698497, 698474

-

1.13.12.17

2 entries

Product in Enzyme-catalyzed Reactions (4 results)

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Show Product (4 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.21.98.2

7-chloroindole-3-pyruvic acid + 7-chlorotryptophan + O2 = 11,11'-dichlorochromopyrrolic acid + NH3 + H2O

0

-

1.21.98.2

4 2-imino-3-(7-chloroindol-3-yl)propanoate + O2 = 2 dichlorochromopyrrolate + 2 NH3 + 2 H2O

0

-

1.21.98.2

2 3-(7-chloroindol-3-yl)-2-iminopropanoate + H2O2 = dichlorochromopyrrolate + NH3 + 2 H2O

0

-

1.21.98.2

2-imino-3-(7-chloroindol-3-yl)propanoate + O2 = dichlorochromopyrrolate + NH3 + H2O

0

-

1.21.98.2

4 entries

Enzyme Kinetic Parameters

References & Links

Literature References (5)

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Show Reference (5 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

698452

16967980

Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid

2006

Howard-Jones, A.R.; Walsh, C.T.

J. Am. Chem. Soc.

128

12289-12298

698455

17705392

Nonenzymatic oxidative steps accompanying action of the cytochrome P450 enzymes StaP and RebP in the biosynthesis of staurosporine and rebeccamycin

2007

Howard-Jones, A.R.; Walsh, C.T.

J. Am. Chem. Soc.

129

11016-11007

698474

18481854

Electron transfer activation of chromopyrrolic acid by cytochrome P450 en route to the formation of an antitumor indolocarbazole derivative: theory supports experiment

2008

Wang, Y.; Hirao, H.; Chen, H.; Onaka, H.; Nagano, S.; Shaik, S.

J. Am. Chem. Soc.

130

7170-7171

698497

19385626

Theoretical and experimental studies of the conversion of chromopyrrolic acid to an antitumor derivative by cytochrome P450 StaP: the catalytic role of water molecules

2009

Wang, Y.; Chen, H.; Makino, M.; Shiro, Y.; Nagano, S.; Asamizu, S.; Onaka, H.; Shaik, S.

J. Am. Chem. Soc.

131

6748-6762

700932

17606921

Crystal structures and catalytic mechanism of cytochrome P450 StaP that produces the indolocarbazole skeleton

2007

Makino, M.; Sugimoto, H.; Shiro, Y.; Asamizu, S.; Onaka, H.; Nagano, S.

Proc. Natl. Acad. Sci. USA

104

11591-11596

Links to other databases for dichlorochromopyrrolate

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Show Links (1 entry)

ChEBI

PubChem