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Literature summary for 4.2.1.127 extracted from
- (De)hydratases-recent developments and future perspectives (2018), Curr. Opin. Chem. Biol., 43, 43-50 .
Activating Compound
| Activating Compound | Comment | Organism | Structure |
|---|---|---|---|
| DMSO | 10% v/v | Castellaniella defragrans |  |
Cloned(Commentary)
| Cloned (Comment) | Organism |
|---|---|
| gene ldi, DNA and amino acid sequence determination and analysis | Castellaniella defragrans |
Inhibitors
| Inhibitors | Comment | Organism | Structure |
|---|---|---|---|
| additional information | no inhibition by EDTA | Castellaniella defragrans |
Localization
| Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|
| periplasm | the enzyme sequence includes an N-terminal signal peptide of 27 amino acids suggesting that LinD is naturally transported into the periplasm | Castellaniella defragrans | - |
- |
Metals/Ions
| Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|
| additional information | the enzyme does not require metal atoms | Castellaniella defragrans |
Natural Substrates/ Products (Substrates)
| Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (3S)-linalool | Castellaniella defragrans | LinD enantioselectively transforms beta-myrcene to (S)-(+)-linalool (coriandrol) with an enantiomeric excess of at least 95.4% | beta-myrcene + H2O | - |
r | |
| (3S)-linalool | Castellaniella defragrans 65Phen | LinD enantioselectively transforms beta-myrcene to (S)-(+)-linalool (coriandrol) with an enantiomeric excess of at least 95.4% | beta-myrcene + H2O | - |
r | |
| additional information | Castellaniella defragrans | the bifunctional linalool dehydratase isomerase (LinD) catalyzes the isomerization of geraniol to linalool, EC 5.4.4.4, and likewise the dehydration of linalool to myrcene, EC 4.2.1.127. No activity with alpha-ocimene and beta-ocimene as well as citronellol and nerol. LinD accepts a broad variety of elongated and truncated aliphatic and even aromatic tertiary alcohols (C5-C15) providing chiral dehydration products with selectivity factors of up to 200. Substrates lacking the signature motif are not accepted by LinD | ? | - |
? | |
| additional information | Castellaniella defragrans 65Phen | the bifunctional linalool dehydratase isomerase (LinD) catalyzes the isomerization of geraniol to linalool, EC 5.4.4.4, and likewise the dehydration of linalool to myrcene, EC 4.2.1.127. No activity with alpha-ocimene and beta-ocimene as well as citronellol and nerol. LinD accepts a broad variety of elongated and truncated aliphatic and even aromatic tertiary alcohols (C5-C15) providing chiral dehydration products with selectivity factors of up to 200. Substrates lacking the signature motif are not accepted by LinD | ? | - |
? | |
Organism
| Organism | UniProt | Comment | Textmining |
|---|---|---|---|
| Castellaniella defragrans | E1XUJ2 | - |
- |
| Castellaniella defragrans 65Phen | E1XUJ2 | - |
- |
Purification (Commentary)
| Purification (Comment) | Organism |
|---|---|
| native enzyme LinD out of crude extracts of strain 65Phen with a yield of 0.02% of the total soluble extract | Castellaniella defragrans |
Reaction
| Reaction | Comment | Organism | Reaction ID |
|---|---|---|---|
| (3S)-linalool = myrcene + H2O | reaction mechanism via one acid-base mechanism via a carbocation intermediate. Residues C171, Y45 and D39 act as general acid and base for the protonation of the hydroxyl leaving group of the substrate (S)-linalool and the dehydration at the chiral carbon atom. Water is activated by H129 or C180 and added to the covalent or carbocation intermediate | Castellaniella defragrans |
Specific Activity [micromol/min/mg]
| Specific Activity Minimum [µmol/min/mg] | Specific Activity Maximum [µmol/min/mg] | Comment | Organism |
|---|---|---|---|
| 0.00087 | - |
partially purified native enzyme, pH 8.0, 35°C, dehydratase activity | Castellaniella defragrans |
Substrates and Products (Substrate)
| Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|
| (3S)-linalool | - |
Castellaniella defragrans | beta-myrcene + H2O | - |
r | |
| (3S)-linalool | LinD enantioselectively transforms beta-myrcene to (S)-(+)-linalool (coriandrol) with an enantiomeric excess of at least 95.4% | Castellaniella defragrans | beta-myrcene + H2O | - |
r | |
| (3S)-linalool | - |
Castellaniella defragrans 65Phen | beta-myrcene + H2O | - |
r | |
| (3S)-linalool | LinD enantioselectively transforms beta-myrcene to (S)-(+)-linalool (coriandrol) with an enantiomeric excess of at least 95.4% | Castellaniella defragrans 65Phen | beta-myrcene + H2O | - |
r | |
| additional information | the bifunctional linalool dehydratase isomerase (LinD) catalyzes the isomerization of geraniol to linalool, EC 5.4.4.4, and likewise the dehydration of linalool to myrcene, EC 4.2.1.127. No activity with alpha-ocimene and beta-ocimene as well as citronellol and nerol. LinD accepts a broad variety of elongated and truncated aliphatic and even aromatic tertiary alcohols (C5-C15) providing chiral dehydration products with selectivity factors of up to 200. Substrates lacking the signature motif are not accepted by LinD | Castellaniella defragrans | ? | - |
? | |
| additional information | the bifunctional linalool dehydratase isomerase (LinD) catalyzes the isomerization of geraniol to linalool, EC 5.4.4.4, and likewise the dehydration of linalool to myrcene, EC 4.2.1.127. No activity with alpha-ocimene and beta-ocimene as well as citronellol and nerol. LinD accepts a broad variety of elongated and truncated aliphatic and even aromatic tertiary alcohols (C5-C15) providing chiral dehydration products with selectivity factors of up to 200. Substrates lacking the signature motif are not accepted by LinD | Castellaniella defragrans 65Phen | ? | - |
? | |
Subunits
| Subunits | Comment | Organism |
|---|---|---|
| homotetramer | 4 * 40000, SDS-PAGE | Castellaniella defragrans |
Synonyms
| Synonyms | Comment | Organism |
|---|---|---|
| LDI | - |
Castellaniella defragrans |
| linalool dehydratase isomerase | - |
Castellaniella defragrans |
| LinD | - |
Castellaniella defragrans |
Temperature Optimum [°C]
| Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|
| 35 | - |
- |
Castellaniella defragrans |
pH Optimum
| pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|
| 8 | - |
- |
Castellaniella defragrans |
pH Range
| pH Minimum | pH Maximum | Comment | Organism |
|---|---|---|---|
| additional information | - |
pH optimum at low alkaline pH, showing a massive drop at pH beyond pH 9.0 | Castellaniella defragrans |
General Information
| General Information | Comment | Organism |
|---|---|---|
| metabolism | the enzyme is responsible for the first two steps in myrcene degradation in Castellaniella defragrans as geraniol is further oxidized shifting the reaction equilibrium | Castellaniella defragrans |
| additional information | the active site of the enzyme is proposed to be located at the interface of two neighboring monomers and, therefore, to be made up of amino acid residues M125, C171, C180, H129, Q179 and Y420 from chain A and D39 and Y45 from chain B. Residues Y45, M125, H129, C171 and C180 are involved in the mechanism of the isomerization of geraniol as well as the dehydration of linalool. Reaction mechanisms, one via a covalent intermediate, and one acid-base mechanism via a carbocation intermediate. In both cases, C171, Y45 and D39 act as general acid and base for the protonation of the hydroxyl leaving group of the substrate (S)-linalool and the dehydration at the chiral carbon atom. Water is activated by H129 or C180 and added to the covalent or carbocation intermediate | Castellaniella defragrans |
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