KEGG ENZYME: 1.14.14.149

ENZYME: 1.14.14.149

Entry

EC 1.14.14.149              Enzyme

Name

5-epiaristolochene 1,3-dihydroxylase;
5-epi-aristolochene 1,3-dihydroxylase;
EAH;
CYP71D20

Class

Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

Sysname

5-epiaristolochene,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (1- and 3-hydroxylating)

Reaction(IUBMB)

5-epiaristolochene + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = capsidiol + 2 [oxidized NADPH---hemoprotein reductase] + 2 H2O [RN:R09573]

Reaction(KEGG)

R09573

Substrate

5-epiaristolochene [CPD:C19708];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]

Product

capsidiol [CPD:C09627];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]

Comment

A cytochrome P-450 (heme-thiolate) protein. Kinetic studies suggest that 1beta-hydroxyepiaristolochene is mainly formed first followed by hydroxylation at C-3. However the reverse order via 3alpha-hydroxyepiaristolochene does occur.

History

EC 1.14.14.149 created 2011 as EC 1.14.13.119, transferred 2018 to EC 1.14.14.149

Pathway

ec00909

Sesquiterpenoid and triterpenoid biosynthesis

Orthology

K15805

5-epiaristolochene 1,3-dihydroxylase

Genes

SOT:

102602839

SSTN:

125856529

CANN:

107858875

NTA:	107759261(CYP71D20) 107795237 107825018(CYP71D21)

NSY:	104222453 104247522

NTO:

104116297

NAU:	109231983 109237630

Reference

1 [PMID:11556809]

Authors

Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J

Title

Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum).

Journal

Arch Biochem Biophys 393:222-35 (2001)
DOI:10.1006/abbi.2001.2483

Sequence

[ag:AAK62342]

Reference

2 [PMID:15522862]

Authors

Takahashi S, Zhao Y, O'Maille PE, Greenhagen BT, Noel JP, Coates RM, Chappell J

Title

Kinetic and molecular analysis of 5-epiaristolochene 1,3-dihydroxylase, a cytochrome P450 enzyme catalyzing successive hydroxylations of sesquiterpenes.

Journal

J Biol Chem 280:3686-96 (2005)
DOI:10.1074/jbc.M411870200

Sequence

[ag:AAK62342]

Other DBs

ExplorEnz - The Enzyme Database:

1.14.14.149

IUBMB Enzyme Nomenclature:

1.14.14.149

ExPASy - ENZYME nomenclature database:

1.14.14.149

BRENDA, the Enzyme Database:

1.14.14.149

DBGET integrated database retrieval system