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4.2.3.52

Accepted name:

(4S)-β-phellandrene synthase (geranyl-diphosphate-cyclizing)

Reaction:

geranyl diphosphate = (4S)-β-phellandrene + diphosphate

For diagram of menthane monoterpenoid biosynthesis, click here

Other name(s):

phellandrene synthase; (-)-β-phellandrene synthase; (-)-(4S)-β-phellandrene synthase

Systematic name:

geranyl-diphosphate diphosphate-lyase [cyclizing; (4S)-β-phellandrene-forming]

Comments:

Requires Mn²⁺. Mg²⁺ is not effective [1]. Some (-)-α-phellandrene is also formed [3]. The reaction involves a 1,3-hydride shift [4].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number: 137010-34-5

References:

1.	Savage, T.J., Hatch, M.W. and Croteau, R. Monoterpene synthases of Pinus contorta and related conifers. A new class of terpenoid cyclase. J. Biol. Chem. 269 (1994) 4012–4020. [PMID: 8307957]
2.	Bohlmann, J., Phillips, M., Ramachandiran, V., Katoh, S. and Croteau, R. cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis). Arch. Biochem. Biophys. 368 (1999) 232–243. [DOI] [PMID: 10441373]
3.	Wagschal, K., Savage, T.J. and Croteau, R. Isotopically sensitive branching as a tool for evaluating multiple product formation by monoterpene cyclases. Tetrahedron 31 (1991) 5933–5944.
4.	LaFever, R.E. and Croteau, R. Hydride shifts in the biosynthesis of the p-menthane monoterpenes α-terpinene, γ-terpinene, and β-phellandrene. Arch. Biochem. Biophys. 301 (1993) 361–366. [DOI] [PMID: 8460944]

[EC 4.2.3.52 created 2010]

4.2.3.114

Accepted name:

γ-terpinene synthase

Reaction:

geranyl diphosphate = γ-terpinene + diphosphate

For diagram of menthane monoterpenoid biosynthesis, click here

Glossary:

γ-terpinene = 1-isopropyl-4-methylcyclohexa-1,4-diene

Other name(s):

OvTPS2; ClcTS

Systematic name:

geranyl-diphosphate diphosphate-lyase (cyclizing, γ-terpinene-forming)

Comments:

Isolated from Thymus vulgaris (thyme) [1,2], Citrus limon (lemon) [3], Citrus unshiu (satsuma) [4] and Origanum vulgare (oregano) [5]. Requires Mg²⁺. Mn²⁺ less effective. The reaction involves a 1,2-hydride shift. The 5-pro-S hydrogen of geranyl diphosphate is lost. Traces of several other monoterpenoids are formed in addition to γ-terpinene.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Alonso, W.R. and Croteau, R. Purification and characterization of the monoterpene cyclase γ-terpinene synthase from Thymus vulgaris. Arch. Biochem. Biophys. 286 (1991) 511–517. [DOI] [PMID: 1897973]
2.	LaFever, R.E. and Croteau, R. Hydride shifts in the biosynthesis of the p-menthane monoterpenes α-terpinene, γ-terpinene, and β-phellandrene. Arch. Biochem. Biophys. 301 (1993) 361–366. [DOI] [PMID: 8460944]
3.	Lücker, J., El Tamer, M.K., Schwab, W., Verstappen, F.W., van der Plas, L.H., Bouwmeester, H.J. and Verhoeven, H.A. Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases. Eur. J. Biochem. 269 (2000) 3160–3171. [DOI] [PMID: 12084056]
4.	Suzuki, Y., Sakai, H., Shimada, T., Omura, M., Kumazawa, S. and Nakayama, T. Characterization of γ-terpinene synthase from Citrus unshiu (Satsuma mandarin). Biofactors 21 (2004) 79–82. [PMID: 15630174]
5.	Crocoll, C., Asbach, J., Novak, J., Gershenzon, J. and Degenhardt, J. Terpene synthases of oregano (Origanum vulgare L.) and their roles in the pathway and regulation of terpene biosynthesis. Plant Mol. Biol. 73 (2010) 587–603. [DOI] [PMID: 20419468]

[EC 4.2.3.114 created 2012]

4.2.3.115

Accepted name:

α-terpinene synthase

Reaction:

geranyl diphosphate = α-terpinene + diphosphate

For diagram of menthane monoterpenoid biosynthesis, click here

Glossary:

α-terpinene = 1-isopropyl-4-methylcyclohexa-1,3-diene

Systematic name:

geranyl-diphosphate diphosphate-lyase (cyclizing, α-terpinene-forming)

Comments:

The enzyme has been characterized from Dysphania ambrosioides (American wormseed). Requires Mg²⁺. Mn²⁺ is less effective. The enzyme will also use (3R)-linalyl diphosphate. The reaction involves a 1,2-hydride shift. The 1-pro-S hydrogen of geranyl diphosphate is lost.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Poulose, A.J. and Croteau, R. γ-Terpinene synthetase: a key enzyme in the biosynthesis of aromatic monoterpenes. Arch. Biochem. Biophys. 191 (1978) 400–411. [DOI] [PMID: 736574]
2.	LaFever, R.E. and Croteau, R. Hydride shifts in the biosynthesis of the p-menthane monoterpenes α-terpinene, γ-terpinene, and β-phellandrene. Arch. Biochem. Biophys. 301 (1993) 361–366. [DOI] [PMID: 8460944]

[EC 4.2.3.115 created 2012]

4.2.3.177

Accepted name:

β-thujene synthase

Reaction:

geranyl diphosphate = β-thujene + diphosphate

For diagram of thujane monoterpenoid biosynthesis, click here

Other name(s):

CoTPS1

Systematic name:

geranyl-diphosphate diphosphate-lyase (cyclizing, β-thujene-forming)

Comments:

Isolated from the plant Cananga odorata var. fruticosa (ylang ylang). The enzyme forms roughly equal proportions of β-thujene, sabinene, β-pinene and α-terpinene see EC 4.2.3.109/EC 4.2.3.110 sabinene synthase, EC 4.2.3.120/EC 4.2.3.122 β-pinene synthase, EC 4.2.3.115 α-terpinene synthase.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

Jin, J., Kim, M.J., Dhandapani, S., Tjhang, J.G., Yin, J.L., Wong, L., Sarojam, R., Chua, N.H. and Jang, I.C. The floral transcriptome of ylang ylang (Cananga odorata var. fruticosa) uncovers biosynthetic pathways for volatile organic compounds and a multifunctional and novel sesquiterpene synthase. J. Exp. Bot. 66 (2015) 3959–3975. [DOI] [PMID: 25956881]

[EC 4.2.3.177 created 2017]