KEGG ENZYME: 1.3.1.100

ENZYME: 1.3.1.100

Entry

EC 1.3.1.100                Enzyme

Name

chanoclavine-I aldehyde reductase;
FgaOx3;
easA (gene name)

Class

Oxidoreductases;
Acting on the CH-CH group of donors;
With NAD+ or NADP+ as acceptor

Sysname

chanoclavine-I aldehyde:NAD+ oxidoreductase

Reaction(IUBMB)

dihydrochanoclavine-I aldehyde + NADP+ = chanoclavine-I aldehyde + NADPH + H+ [RN:R12090]

Reaction(KEGG)

R12090

Substrate

dihydrochanoclavine-I aldehyde [CPD:C21897];
NADP+ [CPD:C00006]

Product

chanoclavine-I aldehyde [CPD:C20379];
NADPH [CPD:C00005];
H+ [CPD:C00080]

Comment

Contains FMN. The enzyme participates in the biosynthesis of fumigaclavine C, an ergot alkaloid produced by some fungi of the Trichocomaceae family. The enzyme catalyses the reduction of chanoclavine-I aldehyde to dihydrochanoclavine-I aldehyde. This hydrolyses spontaneously to form 6,8-dimethyl-6,7-didehydroergoline, which is converted to festuclavine by EC 1.5.1.44, festuclavine dehydrogenase.

History

EC 1.3.1.100 created 2013

Pathway

ec00901

Indole alkaloid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K19182

chanoclavine-I aldehyde reductase

Genes

MAW:	19251292(J3458_016185)

MAJ:

MAA_06743

MBRN:

26246257(G6M90_00g054530)

GLZ:	GLAREA_05926

AFM:	AFUA_2G17960

Reference

1 [PMID:20435769]

Authors

Coyle CM, Cheng JZ, O'Connor SE, Panaccione DG

Title

An old yellow enzyme gene controls the branch point between Aspergillus fumigatus and Claviceps purpurea ergot alkaloid pathways.

Journal

Appl Environ Microbiol 76:3898-903 (2010)
DOI:10.1128/AEM.02914-09

Sequence

[afm:AFUA_2G17960]

Reference

2 [PMID:20102147]

Authors

Cheng JZ, Coyle CM, Panaccione DG, O'Connor SE

Title

A role for Old Yellow Enzyme in ergot alkaloid biosynthesis.

Journal

J Am Chem Soc 132:1776-7 (2010)
DOI:10.1021/ja910193p

Reference

3 [PMID:20526482]

Authors

Wallwey C, Matuschek M, Xie XL, Li SM

Title

Ergot alkaloid biosynthesis in Aspergillus fumigatus: Conversion of chanoclavine-I aldehyde to festuclavine by the festuclavine synthase FgaFS in the presence of the old yellow enzyme FgaOx3.

Journal

Org Biomol Chem 8:3500-8 (2010)
DOI:10.1039/c003823g

Sequence

[afm:AFUA_2G17960]

Reference

4 [PMID:21898587]

Authors

Xie X, Wallwey C, Matuschek M, Steinbach K, Li SM

Title

Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation.

Journal

Magn Reson Chem 49:678-81 (2011)
DOI:10.1002/mrc.2796

Sequence

[afm:AFUA_2G17960]

Other DBs

ExplorEnz - The Enzyme Database:

1.3.1.100

IUBMB Enzyme Nomenclature:

1.3.1.100

ExPASy - ENZYME nomenclature database:

1.3.1.100

BRENDA, the Enzyme Database:

1.3.1.100

DBGET integrated database retrieval system