BRENDA home
History
Information on EC 4.2.3.111 - (-)-alpha-terpineol synthase
for references in articles please use BRENDA:EC4.2.3.111Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree
4.2.3.111 (-)-alpha-terpineol synthaseIUBMB Comments
The enzyme has been characterized from Vitis vinifera (grape). Also forms some 1,8-cineole and traces of other monoterpenoids.
Specify your search results
The enzyme appears in viruses and cellular organisms
Synonyms
alpha-terpineol synthase, alpha-terpineol synthase 2, alpha-TPS, Tctps5, TER, terpene synthase 5, TES2, 
more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alpha-terpineol synthase
alpha-terpineol synthase 2
TES2
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate + H2O = (-)-alpha-terpineol + diphosphate
-
-
-
-
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PATHWAY SOURCE
PATHWAYS
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-alpha-terpineol-forming]
The enzyme has been characterized from Vitis vinifera (grape). Also forms some 1,8-cineole and traces of other monoterpenoids.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(-)-alpha-terpineol + diphosphate
-
products are 50.1% (-)-alpha-terpineol, 11.8% 1,8-cineole, 8.5% (+)-beta-pinene, plus lower amounts of additional monoterpenes
-
?
geranyl diphosphate + H2O
(-)-alpha-terpineol + diphosphate
-
-
-
?
geranyl diphosphate + H2O
(-)-alpha-terpineol + diphosphate
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
-
-
?
geranyl diphosphate + H2O
alpha-terpineol + diphosphate
-
the stereochemistry is not specified in the publication
-
-
?
geranyl diphosphate + H2O
alpha-terpineol + diphosphate
-
the stereochemistry is not specified in the publication
-
-
?
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
-
-
?
additional information
?
-
no substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
additional information
?
-
-
no substrates: farnesyl diphosphate, geranylgeranyl diphosphate
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate + H2O
(-)-alpha-terpineol + diphosphate
-
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
distribution of alpha-terpineol content in the 61 grapevine accessions
brenda
additional information
-
strongest signals with RNA from flower buds and strongly reduced transcript levels in pre- and postanthesis open flowers and in set flowers at early fruit onset
brenda
-
strongest signals with RNA from flower buds and strongly reduced transcript levels in pre- and postanthesis open flowers and in set flowers at early fruit onset
-
brenda
additional information
-
expression appears restricted to flowers
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
distribution of alpha-terpineol content in the 61 grapevine accessions
malfunction
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
physiological function
alpha-terpineol is one of the main monoterpenes found in the grape berry (Vitis vinifera) with its concentrations varying in different varieties. Identification of associations between the alpha-terpineol synthase (alpha-TPS) gene, a regulator of alpha-terpineol metabolism, and alpha-terpineol content in different grapevine varieties
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
malfunction
-
oleocellosis is a serious physiological disorder in citrus fruit that mainly results in appearance and quality deterioration. Large changes in the volatile profiles and gene expression in terpenoid metabolism are observed in oleocellosis peels compared to healthy ones. For gene expressions in terpenoid metabolism, the upregulated genes aldehyde dehydrogenase (NAD+) (ALDH) and the downregulated genes beta-caryophyllene synthase 1 (BCS1), alpha-terpineol synthase 2 (TES2), and myrcene synthase (MS) are the main differences in oleocellosis peels
malfunction
-
oleocellosis is a serious physiological disorder in citrus fruit that mainly results in appearance and quality deterioration. Large changes in the volatile profiles and gene expression in terpenoid metabolism are observed in oleocellosis peels compared to healthy ones. For gene expressions in terpenoid metabolism, the upregulated genes aldehyde dehydrogenase (NAD+) (ALDH) and the downregulated genes beta-caryophyllene synthase 1 (BCS1), alpha-terpineol synthase 2 (TES2), and myrcene synthase (MS) are the main differences in oleocellosis peels
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). ATESY_MAGGA
592
0
67904
Swiss-Prot
Chloroplast (Reliability: 2)
ATESY_VITVI
590
0
68883
Swiss-Prot
Chloroplast (Reliability: 2)
PT10_PINTA
627
0
71884
Swiss-Prot
Chloroplast (Reliability: 2)
TPS26_MAIZE
627
0
70785
Swiss-Prot
Chloroplast (Reliability: 2)
A0A5B7B8Q7_DAVIN
193
0
22608
TrEMBL
Chloroplast (Reliability: 2)
A0A5B7B4V6_DAVIN
590
0
69051
TrEMBL
Chloroplast (Reliability: 3)
A0A5B7B5E6_DAVIN
517
0
60667
TrEMBL
Chloroplast (Reliability: 2)
A0A2G9GEB1_9LAMI
574
0
67567
TrEMBL
Mitochondrion (Reliability: 2)
A0A2G9HSG2_9LAMI
413
0
48964
TrEMBL
Mitochondrion (Reliability: 4)
A0A5B7B645_DAVIN
391
0
45827
TrEMBL
other Location (Reliability: 2)
A0A5B7B4U1_DAVIN
498
0
58346
TrEMBL
other Location (Reliability: 3)
A0A5B7B5P9_DAVIN
595
0
69385
TrEMBL
Chloroplast (Reliability: 2)
A0A2G9HM99_9LAMI
600
0
70742
TrEMBL
Mitochondrion (Reliability: 4)
A0A5B7B6J1_DAVIN
605
0
70743
TrEMBL
Chloroplast (Reliability: 2)
A0A5B7B4K8_DAVIN
290
0
33486
TrEMBL
other Location (Reliability: 3)
A0A5B7B4A8_DAVIN
498
0
58790
TrEMBL
Chloroplast (Reliability: 3)
A0A5B7BW53_DAVIN
595
0
68791
TrEMBL
Chloroplast (Reliability: 2)
A0A2G9HSN5_9LAMI
600
0
70609
TrEMBL
other Location (Reliability: 4)
A0A2G9GL89_9LAMI
603
0
69831
TrEMBL
Chloroplast (Reliability: 3)
A0A2G9HPL9_9LAMI
603
0
69872
TrEMBL
Chloroplast (Reliability: 3)
V5JYL0_THYVU
597
0
69178
TrEMBL
Chloroplast (Reliability: 1)
A0A5B7B820_DAVIN
498
0
58157
TrEMBL
other Location (Reliability: 3)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A147R/A148N
site-directed mutagenesis, the mutation leads to an altered monoterpenes profile compared to wild-type
A277T/A147R/A148N
site-directed mutagenesis, the mutation leads to an altered monoterpenes profile compared to wild-type
S264F
site-directed mutagenesis, the mutation leads to an altered monoterpenes profile compared to wild-type
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged wild-type enzyme from Escherichia coli strain HMS 174(DE3) by nickel affinity chromatography
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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)
gene TES2, quantitative expression analysis
genotyping and identification of single nuclaer polymorphisms in the gene
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enyzme encoded by TES2 gene is significantly downregulated in oleocellosis, a Citrus physiological disorder
the enyzme encoded by TES2 gene is significantly downregulated in oleocellosis, a Citrus physiological disorder
-
the enyzme encoded by TES2 gene is significantly downregulated in oleocellosis, a Citrus physiological disorder
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Luecker, J.; Bowen, P.; Bohlmann, J.
Vitis vinifera terpenoid cyclases: functional identification of two sesquiterpene synthase cDNAs encoding (+)-valencene synthase and (-)-germacrene D synthase and expression of mono- and sesquiterpene synthases in grapevine flowers and berries
Phytochemistry
65
2649-2659
2004
Vitis vinifera
brenda
Martin, D.M.; Bohlmann, J.
Identification of Vitis vinifera (-)-alpha-terpineol synthase by in silico screening of full-length cDNA ESTs and functional characterization of recombinant terpene synthase
Phytochemistry
65
1223-1229
2004
Vitis vinifera (Q6PWU2), Vitis vinifera
brenda
Yang, X.; Guo, Y.; Zhu, J.; Ma, N.; Sun, T.; Liu, Z.; Li, K.; Guo, X.
Associations between the alpha-terpineol synthase gene and alpha-terpineol content in different grapevine varieties
Biotechnol. Biotechnol. Equip.
31
1100-1105
2017
Vitis vinifera (Q6PWU2)
-
brenda
Xie, J.; Deng, L.; Zhou, Y.; Yao, S.; Zeng, K.
Analysis of changes in volatile constituents and expression of genes involved in terpenoid metabolism in oleocellosis peel
Food Chem.
243
269-276
2018
Citrus reticulata, Citrus sinensis
brenda
Mirzaei, F.; Fatehi, F.; Ismaili, A.; Yaghotipoor, A.; Qaderi, A.
Expression of genes 1-deoxy-D-xylulose 5-phosphate reductoisomerase (DXR), sabinene synthase (Tctps1) and alpha-terpineol synthase (Tctps5) and its relation to thymol and carvacrol biosynthesis in Thymus vulgaris under water deficit stress
J. Med. Plants
16
58-70
2017
Thymus vulgaris (V5JYL0)
-
brenda
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
Plant Physiol.
172
2120-2131
2016
Nicotiana langsdorffii (H2ELN1)
brenda
Select items on the left to see more content.
EXTERNAL LINKS (specific for EC-Number 4.2.3.111)
html completed
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
About BRENDA
Help
Download
Contribution
member of
curated at
curated at
Server: brenda1 Ver: 9edf756-main (2022-05-17 10:30:03 +0200)