1,8-cineole synthase

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1,8-cineole synthase
Identifiers
EC no. 4.2.3.108
CAS no. 110637-19-9
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1,8-Cineole synthase (EC 4.2.3.108, 1,8-cineole cyclase, geranyl pyrophoshate:1,8-cineole cyclase, 1,8-cineole synthetase) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase (cyclizing, 1,8-cineole-forming). [1] [2] [3] [4] [5] This enzyme catalyses the following chemical reaction

geranyl diphosphate + H2O 1,8-cineole + diphosphate
Eucalyptol synthesis.svg

This enzyme requires Mn2+ or Zn2+. Geranyl diphosphate first isomerizes to (S)-linalyl diphosphate which ionises to the alpha-terpinyl cation which reacts with water to form the product. [6]

Related Research Articles

<span class="mw-page-title-main">Eucalyptol</span> Chemical compound

Eucalyptol is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

<span class="mw-page-title-main">Sabinene</span> Chemical compound

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids. It is also used in the synthesis of CoQ, as well as dehydrodolichol diphosphate.

<span class="mw-page-title-main">Bornyl diphosphate synthase</span>

In enzymology, bornyl diphosphate synthase (BPPS) (EC 5.5.1.8) is an enzyme that catalyzes the chemical reaction

The enzyme (4S)-limonene synthase catalyzes the chemical reaction

In enzymology, a pinene synthase is an enzyme that catalyzes the chemical reaction

The enzyme (R)-limonene synthase (EC 4.2.3.20) catalyzes the reversible chemical reaction

The enzyme sabinene-hydrate synthase (EC 4.2.3.11) catalyzes the chemical reaction

β-Phellandrene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

(+)-Car-3-ene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]. This enzyme catalyses the following chemical reaction

(–)-Sabinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-sabinene-forming]. This enzyme catalyses the following chemical reaction

(+)-Sabinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-sabinene-forming]. This enzyme catalyses the following chemical reaction

Terpinolene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

γ-Terpinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

(+)-camphene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-camphene-forming]. This enzyme catalyses the following chemical reaction

(–)-camphene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-camphene-forming]. This enzyme catalyses the following chemical reaction

(–)-α-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

(–)-β-Pinene synthase (EC 4.2.3.120, β-geraniolene synthase, (–)-(1S,5S)-pinene synthase, geranyldiphosphate diphosphate lyase (pinene forming)) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-β-pinene-forming]. This enzyme catalyses the following chemical reaction

(+)-α-pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

(+)-β-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [(+)-β-pinene-forming]. This enzyme catalyses the following chemical reaction

References

  1. Croteau R, Alonso WR, Koepp AE, Johnson MA (February 1994). "Biosynthesis of monoterpenes: partial purification, characterization, and mechanism of action of 1,8-cineole synthase". Archives of Biochemistry and Biophysics. 309 (1): 184–192. doi:10.1006/abbi.1994.1101. PMID   8117108.
  2. Wise ML, Savage TJ, Katahira E, Croteau R (June 1998). "Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase". The Journal of Biological Chemistry. 273 (24): 14891–14899. doi: 10.1074/jbc.273.24.14891 . PMID   9614092.
  3. Peters RJ, Croteau RB (September 2003). "Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases". Archives of Biochemistry and Biophysics. 417 (2): 203–211. doi:10.1016/s0003-9861(03)00347-3. PMID   12941302.
  4. Chen F, Ro DK, Petri J, Gershenzon J, Bohlmann J, Pichersky E, Tholl D (August 2004). "Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole". Plant Physiology. 135 (4): 1956–1966. doi:10.1104/pp.104.044388. PMC   520767 . PMID   15299125.
  5. Keszei A, Brubaker CL, Carter R, Köllner T, Degenhardt J, Foley WJ (June 2010). "Functional and evolutionary relationships between terpene synthases from Australian Myrtaceae". Phytochemistry. 71 (8–9): 844–852. Bibcode:2010PChem..71..844K. doi:10.1016/j.phytochem.2010.03.013. PMID   20399476.
  6. Rinkel J, Rabe P, Zur Horst L, Dickschat JS (2016-11-04). "A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus". Beilstein Journal of Organic Chemistry. 12: 2317–2324. doi:10.3762/bjoc.12.225. PMC   5238540 . PMID   28144299.