KEGG ENZYME: 4.2.3.227

ENZYME: 4.2.3.227

Entry

EC 4.2.3.227                Enzyme

Name

(-)-alpha-cedrene synthase;
EAS3 (gene name);
EAS4 (gene name)

Class

Lyases;
Carbon-oxygen lyases;
Acting on phosphates

Sysname

(2Z,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, (-)-alpha-cedrene-forming)

Reaction(IUBMB)

(2Z,6E)-farnesyl diphosphate = (-)-alpha-cedrene + diphosphate [RN:R13311]

Reaction(KEGG)

R13311

Substrate

(2Z,6E)-farnesyl diphosphate [CPD:C16826]

Product

(-)-alpha-cedrene [CPD:C22909];
diphosphate [CPD:C00013]

Comment

The enzyme occurs in plants. The initial cyclization product is a (7R)-beta-bisabolyl cation. (-)-alpha-Cedrene is one of the major products. Other products are (+)-2-epi-prezizaene (cf. EC 4.2.3.226, (+)-2-epi-prezizaene synthase), small amounts of (+)-beta-curcumene, and other sesquiterpenes with less than 10% yield. The enzyme from Nicotiana tabacum (tobacco) also catalyses the reaction of EC 4.2.3.61, 5-epiaristolochene synthase.

History

EC 4.2.3.227 created 2024

Reference

1 [PMID:20175559]

Authors

Noel JP, Dellas N, Faraldos JA, Zhao M, Hess BA Jr, Smentek L, Coates RM, O'Maille PE.

Title

Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates.

Journal

ACS Chem Biol 5:377-92 (2010)
DOI:10.1021/cb900295g

Sequence

[ag:AAA19216]