KEGG ORTHOLOGY: K12928

ORTHOLOGY: K12928

Entry

K12928            Tight     KO

Symbol

K12928, ACS

Name

aphidicolan-16beta-ol synthase/syn-copalyl-diphosphate synthase [EC:4.2.3.42 5.5.1.14]

Pathway

map00904

Diterpenoid biosynthesis

map01110

Biosynthesis of secondary metabolites

Reaction

R06312

9alpha-copalyl-diphosphate lyase (decyclizing)

R06313

9alpha-copalyl-diphosphate diphosphate-lyase (aphidicolan-16beta-ol-forming)

R06314

R06315

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   00904 Diterpenoid biosynthesis
    K12928  K12928, ACS; aphidicolan-16beta-ol synthase/syn-copalyl-diphosphate synthase
Enzymes [BR:ko01000]
4. Lyases
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.42  aphidicolan-16beta-ol synthase
     K12928  K12928, ACS; aphidicolan-16beta-ol synthase/syn-copalyl-diphosphate synthase
5. Isomerases
  5.5  Intramolecular lyases
   5.5.1  Intramolecular lyases (only sub-subclass identified to date)
    5.5.1.14  syn-copalyl-diphosphate synthase
     K12928  K12928, ACS; aphidicolan-16beta-ol synthase/syn-copalyl-diphosphate synthase

Other DBs

GO:	0046567 0051498

Genes

AG:	BAB62102(ACS)

Reference

PMID:11457369

Authors

Oikawa H, Toyomasu T, Toshima H, Ohashi S, Kawaide H, Kamiya Y, Ohtsuka M, Shinoda S, Mitsuhashi W, Sassa T

Title

Cloning and functional expression of cDNA encoding aphidicolan-16 beta-ol synthase: a key enzyme responsible for formation of an unusual diterpene skeleton in biosynthesis of aphidicolin.

Journal

J Am Chem Soc 123:5154-5 (2001)
DOI:10.1021/ja015747j

Sequence

[ag:BAB62102]

Reference

PMID:14745177

Authors

Toyomasu T, Nakaminami K, Toshima H, Mie T, Watanabe K, Ito H, Matsui H, Mitsuhashi W, Sassa T, Oikawa H

Title

Cloning of a gene cluster responsible for the biosynthesis of diterpene aphidicolin, a specific inhibitor of DNA polymerase alpha.

Journal

Biosci Biotechnol Biochem 68:146-52 (2004)
DOI:10.1271/bbb.68.146

Sequence

[ag:BAB62102]

LinkDB

ENZYME: 4.2.3.42

Entry

EC 4.2.3.42                 Enzyme

Name

aphidicolan-16beta-ol synthase;
PbACS

Class

Lyases;
Carbon-oxygen lyases;
Acting on phosphates

Sysname

9alpha-copalyl-diphosphate diphosphate-lyase (aphidicolan-16beta-ol-forming)

Reaction(IUBMB)

9alpha-copalyl diphosphate + H2O = aphidicolan-16beta-ol + diphosphate [RN:R06313]

Reaction(KEGG)

R06313

Substrate

9alpha-copalyl diphosphate [CPD:C11902];
H2O [CPD:C00001]

Product

aphidicolan-16beta-ol [CPD:C11890];
diphosphate [CPD:C00013]

Comment

This is a bifunctional enzyme which also has EC 5.5.1.14 syn-copalyl diphosphate synthase activity. Aphidicolan-16beta-ol is a precursor of aphidicolin, a specific inhibitor of DNA polymerase alpha (EC 2.7.7.7).

History

EC 4.2.3.42 created 2009

Pathway

ec00904

Diterpenoid biosynthesis

ec01110

Biosynthesis of secondary metabolites

Orthology

K12928

aphidicolan-16beta-ol synthase/syn-copalyl-diphosphate synthase

Reference

1 [PMID:11457369]

Authors

Oikawa H, Toyomasu T, Toshima H, Ohashi S, Kawaide H, Kamiya Y, Ohtsuka M, Shinoda S, Mitsuhashi W, Sassa T

Title

Cloning and functional expression of cDNA encoding aphidicolan-16 beta-ol synthase: a key enzyme responsible for formation of an unusual diterpene skeleton in biosynthesis of aphidicolin.

Journal

J Am Chem Soc 123:5154-5 (2001)
DOI:10.1021/ja015747j

Sequence

[ag:BAB62102]

Reference

2 [PMID:14745177]

Authors

Toyomasu T, Nakaminami K, Toshima H, Mie T, Watanabe K, Ito H, Matsui H, Mitsuhashi W, Sassa T, Oikawa H

Title

Cloning of a gene cluster responsible for the biosynthesis of diterpene aphidicolin, a specific inhibitor of DNA polymerase alpha.

Journal

Biosci Biotechnol Biochem 68:146-52 (2004)
DOI:10.1271/bbb.68.146

Sequence

[ag:BAB62102]

Other DBs

ExplorEnz - The Enzyme Database:

4.2.3.42

IUBMB Enzyme Nomenclature:

4.2.3.42

ExPASy - ENZYME nomenclature database:

4.2.3.42

BRENDA, the Enzyme Database:

4.2.3.42

LinkDB

REACTION: R06313

Entry

R06313                      Reaction

Name

9alpha-copalyl-diphosphate diphosphate-lyase (aphidicolan-16beta-ol-forming)

Definition

9alpha-Copalyl diphosphate + H2O <=> Aphidicolan-16beta-ol + Diphosphate

Equation

C11902 + C00001 <=> C11890 + C00013

Reaction class

RC02056

C11890_C11902

Enzyme

4.2.3.42

Pathway

rn00904

Diterpenoid biosynthesis

rn01110

Biosynthesis of secondary metabolites

Brite

Enzymatic reactions [BR:br08201]
4. Lyase reactions
  4.2  Carbon-oxygen lyases
   4.2.3  Acting on phosphates
    4.2.3.42
     R06313  9alpha-Copalyl diphosphate + H2O <=> Aphidicolan-16beta-ol + Diphosphate

Orthology

K12928

aphidicolan-16beta-ol synthase/syn-copalyl-diphosphate synthase [EC:4.2.3.42 5.5.1.14]

Other DBs

RHEA:

26216

LinkDB

DBGET integrated database retrieval system