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Literature summary extracted from
- Stereochemical conversion of C3-vinyl group to 1-hydroxyethyl group in bacteriochlorophyll c by the hydratases BchF and BchV adaptation of green sulfur bacteria to limited-light environments (2015), Mol. Microbiol., 98, 1184-1198 .
Cloned(Commentary)
| EC Number | Cloned (Comment) | Organism |
|---|---|---|
| 4.2.1.165 | gene bchF, phylogenetic analysis, recombinant expression in Escherichia coli strain Bl21(DE3), quantitative RT-PCR expression analysis | Chlorobaculum tepidum |
| 4.2.1.169 | gene bchV, phylogenetic analysis, recombinant expression in Escherichia coli strain Bl21(DE3), quantitative RT-PCR expression analysis | Chlorobaculum tepidum |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 4.2.1.165 | additional information | bchF deletion mutant, mutant phenotype with altered pigment biosynthesis, detailed overview | Chlorobaculum tepidum |
| 4.2.1.169 | additional information | bchV deletion mutant, mutant phenotype with altered pigment biosynthesis, detailed overview | Chlorobaculum tepidum |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide a + H2O | Chlorobaculum tepidum | high activity, preferred substrate | (31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? |  |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide a + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | high activity, preferred substrate | (31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide c + H2O | Chlorobaculum tepidum | - |
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide c + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | low activity, the enzyme converts [E,M], [E,E], [E,P], and [E,I] variants, stereochemistry, overview | (3RS)-3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-isobutyl-12-ethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-propyl-12-ethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(3RS)3-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide a + H2O | Chlorobaculum tepidum | - |
(31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide a + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
(31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide c + H2O | Chlorobaculum tepidum | low activity | (31S)-3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide c + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | low activity | (31S)-3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | high activity, the enzyme converts [E,M], [E,E], [P,E], and [E,I] variants, the [E,E] and [P,E] variants are preferred substrates, stereochemistry, overview | (3RS)-3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-isobutyl-12-ethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-propyl-12-ethyl-bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | - |
(3RS)3-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 4.2.1.165 | Chlorobaculum tepidum | Q8KBL0 | - |
- |
| 4.2.1.165 | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | Q8KBL0 | - |
- |
| 4.2.1.169 | Chlorobaculum tepidum | - |
- |
- |
| 4.2.1.169 | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | - |
- |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide a + H2O | high activity, preferred substrate | Chlorobaculum tepidum | (31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide a + H2O | high activity, preferred substrate | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide c + H2O | - |
Chlorobaculum tepidum | (31RS)3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide c + H2O | - |
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31RS)3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.165 | 3-vinyl bacteriochlorophyllide d + H2O | low activity, the enzyme converts [E,M], [E,E], [E,P], and [E,I] variants, stereochemistry, overview | Chlorobaculum tepidum | (3RS)-3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-isobutyl-12-ethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (31RS)3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | 3-vinyl-8-propyl-12-ethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (3RS)3-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.165 | additional information | in vitro activity measurements with crude enzyme extract | Chlorobaculum tepidum | ? | - |
? | |
| 4.2.1.165 | additional information | in vitro activity measurements with crude enzyme extract | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | ? | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide a + H2O | - |
Chlorobaculum tepidum | (31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide a + H2O | - |
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide c + H2O | low activity | Chlorobaculum tepidum | (31S)-3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide c + H2O | low activity | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31S)-3-(1-hydroxyethyl) bacteriochlorophyllide c | - |
? | |
| 4.2.1.169 | 3-vinyl bacteriochlorophyllide d + H2O | high activity, the enzyme converts [E,M], [E,E], [P,E], and [E,I] variants, the [E,E] and [P,E] variants are preferred substrates, stereochemistry, overview | Chlorobaculum tepidum | (3RS)-3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | (31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-isobutyl-12-ethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (31RS)3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | 3-vinyl-8-propyl-12-ethyl-bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | (3RS)3-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | additional information | in vitro activity measurements with crude enzyme extract | Chlorobaculum tepidum | ? | - |
? | |
| 4.2.1.169 | additional information | in vitro activity measurements with crude enzyme extract | Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 4.2.1.165 | bchF | - |
Chlorobaculum tepidum |
| 4.2.1.169 | BchV | - |
Chlorobaculum tepidum |
Expression
| EC Number | Organism | Comment | Expression |
|---|---|---|---|
| 4.2.1.169 | Chlorobaculum tepidum | transcriptional level of bchV is upregulated at lower light intensity, the Chlorobaculum tepidum adapts to low-light environments by control of the bchV transcription | up |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 4.2.1.165 | malfunction | pigment analyses of the bchF-inactivated mutant, which still has BchV as a sole hydratase, show higher ratios of S-epimeric bacteriochlorophyll c than the wild-type strain, while the bchV-mutant possessing only BchF showed a significant decrease of the S-epimers and accumulations of C3-vinyl BChl c species. In BChl a biosynthesis, the C3-vinyl group of a precursor of BChl a is hydrated by BchF, and the C3-1-hydroxyethyl group is then oxidized to the acetyl moiety by BchC | Chlorobaculum tepidum |
| 4.2.1.165 | metabolism | proposed biosynthetic pathways of bacteriochlorophyllides a and c focused on Chlorobaculum tepidum BchF- and BchV-catalyzed reactions, overview | Chlorobaculum tepidum |
| 4.2.1.165 | physiological function | photosynthetic green sulfur bacteria inhabit anaerobic environments with very low-light conditions. Stereochemical conversion of C3-vinyl group to 1-hydroxyethyl group in bacteriochlorophyll c by the hydratases BchF and BchV (EC 4.2.1.169) for adaptation of green sulfur bacteria to limited-light environments. The pigment possess a hydroxy group at the C31 position that produces a chiral center with R- or S-stereochemistry and the C31-hydroxy group serves as a connecting moiety for the self-aggregation | Chlorobaculum tepidum |
| 4.2.1.169 | malfunction | pigment analyses of the bchF-inactivated mutant, which still has BchV as a sole hydratase, show higher ratios of S-epimeric bacteriochlorophyll c than the wild-type strain, while the bchV-mutant possessing only BchF shows a significant decrease of the S-epimers and accumulations of C3-vinyl BChl c species | Chlorobaculum tepidum |
| 4.2.1.169 | metabolism | proposed biosynthetic pathways of bacteriochlorophyllides a and c focused on Chlorobaculum tepidum BchF- and BchV-catalyzed reactions, overview | Chlorobaculum tepidum |
| 4.2.1.169 | physiological function | photosynthetic green sulfur bacteria inhabit anaerobic environments with very low-light conditions. Stereochemical conversion of C3-vinyl group to 1-hydroxyethyl group in bacteriochlorophyll c by the hydratases BchF and BchV (EC 4.2.1.169) for adaptation of green sulfur bacteria to limited-light environments. The pigment possess a hydroxy group at the C31 position that produces a chiral center with R- or S-stereochemistry and the C31-hydroxy group serves as a connecting moiety for the self-aggregation. Transcriptional level of bchV is upregulated at lower light intensity, the Chlorobaculum tepidum adapts to low-light environments by control of the bchV transcription | Chlorobaculum tepidum |
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