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Literature summary for 4.2.3.111 extracted from

  • Piechulla, B.; Bartelt, R.; Brosemann, A.; Effmert, U.; Bouwmeester, H.; Hippauf, F.; Brandt, W.
    The alpha-terpineol to 1,8-cineole cyclization reaction of tobacco terpene synthases (2016), Plant Physiol., 172, 2120-2131 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 4.2.3.111

Cloned(Commentary)

Cloned (Comment) Organism
gene TER, DNA and amino acid sequence determination and analysis, sequence comparisons, recombinant overexpression of His-tagged wild-type enzyme in Escherichia coli strain HMS 174(DE3) Nicotiana langsdorffii

Protein Variants

Protein Variants Comment Organism
A147R/A148N site-directed mutagenesis, the mutation leads to an altered monoterpenes profile compared to wild-type Nicotiana langsdorffii
A277T/A147R/A148N site-directed mutagenesis, the mutation leads to an altered monoterpenes profile compared to wild-type Nicotiana langsdorffii
S264F site-directed mutagenesis, the mutation leads to an altered monoterpenes profile compared to wild-type Nicotiana langsdorffii

Localization

Localization Comment Organism GeneOntology No. Textmining
chloroplast
-
 Nicotiana langsdorffii 9507
-

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Nicotiana langsdorffii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
geranyl diphosphate + H2O Nicotiana langsdorffii
-
 (-)-alpha-terpineol + diphosphate
-
 ?

Organism

Organism UniProt Comment Textmining
Nicotiana langsdorffii H2ELN1
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged wild-type enzyme from Escherichia coli strain HMS 174(DE3) by nickel affinity chromatography Nicotiana langsdorffii

Reaction

Reaction Comment Organism Reaction ID
geranyl diphosphate + H2O = (-)-alpha-terpineol + diphosphate the substrate geranyl diphosphate is ionized by diphosphate elimination, resulting in the geranyl cation. Subsequently, this cation is converted into the linalyl cation and alpha-terpinyl cation. The intermediate alpha-terpinyl cation is the precursor for all cyclic monoterpenes. alpha-Terpineol is formed after water capture of the alpha-terpinyl cation. A cyclization reaction resulting in 1,8-cineole uses alpha-terpineol as a precursor Nicotiana langsdorffii
a

Source Tissue

Source Tissue Comment Organism Textmining
leaf
-
 Nicotiana langsdorffii
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
geranyl diphosphate + H2O
-
 Nicotiana langsdorffii (-)-alpha-terpineol + diphosphate
-
 ?
geranyl diphosphate + H2O the enzyme releases alpha-terpineol as the main compound as a terpineol synthase (TER). The S to R ratio is 11.2:1 and 10.8:1 in two experimental passages Nicotiana langsdorffii (-)-alpha-terpineol + diphosphate
-
 ?
additional information the formation of alpha-terpineol starts by a nucleophilic attack of water. During this attack, the alpha-terpinyl cation is stabilized by Pi-stacking with a tryptophan side chain (Tryp253). The hypothesized catalytic mechanism of alpha-terpineol-to-1,8-cineole conversion is initiated by a catalytic dyad (His502 and Glu249), acting as a base, and a threonine (Thr278) providing the subsequent rearrangement from terpineol to cineol by catalyzing the autoprotonation of (2S)-2-alpha-terpineol, which is the favored enantiomer product of the recombinant enzymes. Product analysis and quantification by GC-MS Nicotiana langsdorffii ?
-
 ?

Synonyms

Synonyms Comment Organism
TER
-
 Nicotiana langsdorffii

General Information

General Information Comment Organism
metabolism cyclization reactions of monoterpene synthases, overview. Substrate geranyl diphosphate is ionized by diphosphate elimination, resulting in the geranyl cation. Subsequently, this cation is converted into the linalyl cation and alpha-terpinyl cation. The synthesis of the acyclic beta-myrcene might proceed via the geranyl cation or via the linalyl cation by deprotonation. The intermediate alpha-terpinyl cation is the precursor for all cyclic monoterpenes. The 2,7-ring closure results in the pinyl cation, which is deprotonated to synthesize beta-pinene and alpha-pinene. Sabinene, with a cyclopropane ring, is released after two carbocation formations and 2,6-ring closure. alpha-Terpineol is formed after water capture of the alpha-terpinyl cation. Broken lines indicate possible reactions leading to 1,8-cineole. A cyclization reaction resulting in 1,8-cineole uses alpha-terpineol as a precursor Nicotiana langsdorffii
additional information the amino acids at positions 147, 148, and 266 determine the different terpineol-cineole ratios in Nicotiana suaveolens cineole synthase and Nicotiana langsdorffii terpineol synthase Nicotiana langsdorffii