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Literature summary extracted from
- In vitro stereospecific hydration activities of the 3-vinyl group of chlorophyll derivatives by BchF and BchV enzymes involved in bacteriochlorophyll c biosynthesis of green sulfur bacteria (2016), Photosynth. Res., 130, 33-45.
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 4.2.1.169 | chlorosome | - |
Chlorobaculum tepidum | 46858 | - |
Metals/Ions
| EC Number | Metals/Ions | Comment | Organism | Structure |
|---|---|---|---|---|
| 4.2.1.169 | additional information | the central metal of substrates is essential for the BchF reaction | Chlorobaculum tepidum | |
| 4.2.1.169 | additional information | the central metal of substrates is essential for the BchV reaction | Chlorobaculum tepidum |
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 4.2.1.169 | a 3-vinyl bacteriochlorophyllide d + H2O | Chlorobaculum tepidum | enzyme BchV prefers the S-stereoisomer, stereospecific reaction | a 3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? |  |
| 4.2.1.169 | a 3-vinyl bacteriochlorophyllide d + H2O | Chlorobaculum tepidum ATCC 49652 | enzyme BchV prefers the S-stereoisomer, stereospecific reaction | a 3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | additional information | Chlorobaculum tepidum | the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV | ? | - |
? | |
| 4.2.1.169 | additional information | Chlorobaculum tepidum ATCC 49652 | the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV | ? | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 4.2.1.169 | Chlorobaculum tepidum | H2VFK0 | - |
- |
| 4.2.1.169 | Chlorobaculum tepidum | Q8KBL0 | - |
- |
| 4.2.1.169 | Chlorobaculum tepidum ATCC 49652 | H2VFK0 | - |
- |
| 4.2.1.169 | Chlorobaculum tepidum ATCC 49652 | Q8KBL0 | - |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 4.2.1.169 | a 3-vinyl bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum | a 3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | a 3-vinyl bacteriochlorophyllide d + H2O | enzyme BchV prefers the S-stereoisomer, stereospecific reaction | Chlorobaculum tepidum | a 3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | a 3-vinyl bacteriochlorophyllide d + H2O | - |
Chlorobaculum tepidum ATCC 49652 | a 3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | a 3-vinyl bacteriochlorophyllide d + H2O | enzyme BchV prefers the S-stereoisomer, stereospecific reaction | Chlorobaculum tepidum ATCC 49652 | a 3-(1-hydroxyethyl) bacteriochlorophyllide d | - |
? | |
| 4.2.1.169 | additional information | the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV | Chlorobaculum tepidum | ? | - |
? | |
| 4.2.1.169 | additional information | in vitro enzymatic hydration of some 3-vinyl-chlorophyll derivatives with usage of zinc complexes of cyclic tetrapyrroles as the enzymatic substrates alternative to chlorophyll(ide)s chelated with magnesium ion. Recombinant BchF catalyzes stereoselective hydration of zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c or d to the zinc 31R-bacteriopheophorbide c or d homologue, respectively. The enzymatic hydration for the 8-propylated substrate proceeds more slowly than that for the 8-ethylated, and the 8-isobutylated substrate is no longer hydrated. The wild-type strain of Chlorobaculum tepidum gives almost exclusively 31R-epimers of 8-ethyl-12-methyl- and 8,12-diethyl-BChl c, approximately 90% 31R- and 10% 31S-epimers of 8-propyl-12-ethyl-BChl c, and entirely 31S-epimer of 8-isobutyl-12-ethyl-BChl c: 4% 31S-epimers in the total amount of BChl c homologues. The in vivo hydrations might be effective even after the 20-methylation by a methyltransferase, BchU. No activity of BchF in the hydration of the 3-vinyl group of protochlorophyllide a, the porphyrin form of chlorophyllide a. The hydrogenation of the porphyrin to chlorin Pi-system is necessary for the substrate of BchF hydration. In all the BchF-catalyzed reactions, the products are mixtures of the 31R- and 31S-epimers, and the R-epimers are mainly obtained with a lower amount of the S-epimers. The 20-methylated analogue of Zn-3V[E,M]BPheide d, Zn-3V[E,M]BPheide c, is hydrated by BchF and BchV enzymes to give Zn-[E,M]BPheide c | Chlorobaculum tepidum | ? | - |
? | |
| 4.2.1.169 | additional information | in vitro enzymatic hydration of some 3-vinyl-chlorophyll derivatives with usage of zinc complexes of cyclic tetrapyrroles as the enzymatic substrates alternative to chlorophyll(ide)s chelated with magnesium ion. Recombinant BchV catalyzes stereoselective hydration of zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c or d to the zinc 31R-bacteriopheophorbide c or d homologue, respectively, with a slight amount of the 31S-epimeric species. The BchV-hydration gives a relatively larger amount of the 31S-epimers. The in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV. The enzymatic hydration for the 8-propylated substrate proceeds more slowly than that for the 8-ethylated, and the 8-isobutylated substrate is no longer hydrated. The wild-type strain of Chlorobaculum tepidum gives almost exclusively 31R-epimers of 8-ethyl-12-methyl- and 8,12-diethyl-BChl c, approximately 90% 31R- and 10% 31S-epimers of 8-propyl-12-ethyl-BChl c, and entirely 31S-epimer of 8-isobutyl-12-ethyl-BChl c: 4% 31S-epimers in the total amount of BChl c homologues. The in vivo hydrations might be effective even after the 20-methylation by a methyltransferase, BchU. No activity of BchV in the hydration of the 3-vinyl group of protochlorophyllide a, the porphyrin form of chlorophyllide a. The hydrogenation of the porphyrin to chlorin Pi-system is necessary for the substrate of BchV hydration. In all the BchV-catalyzed reactions, the products are mixtures of the 31R- and 31S-epimers, and the R-epimers are mainly obtained with a lower amount of the S-epimers | Chlorobaculum tepidum | ? | - |
? | |
| 4.2.1.169 | additional information | the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV | Chlorobaculum tepidum ATCC 49652 | ? | - |
? | |
| 4.2.1.169 | additional information | in vitro enzymatic hydration of some 3-vinyl-chlorophyll derivatives with usage of zinc complexes of cyclic tetrapyrroles as the enzymatic substrates alternative to chlorophyll(ide)s chelated with magnesium ion. Recombinant BchF catalyzes stereoselective hydration of zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c or d to the zinc 31R-bacteriopheophorbide c or d homologue, respectively. The enzymatic hydration for the 8-propylated substrate proceeds more slowly than that for the 8-ethylated, and the 8-isobutylated substrate is no longer hydrated. The wild-type strain of Chlorobaculum tepidum gives almost exclusively 31R-epimers of 8-ethyl-12-methyl- and 8,12-diethyl-BChl c, approximately 90% 31R- and 10% 31S-epimers of 8-propyl-12-ethyl-BChl c, and entirely 31S-epimer of 8-isobutyl-12-ethyl-BChl c: 4% 31S-epimers in the total amount of BChl c homologues. The in vivo hydrations might be effective even after the 20-methylation by a methyltransferase, BchU. No activity of BchF in the hydration of the 3-vinyl group of protochlorophyllide a, the porphyrin form of chlorophyllide a. The hydrogenation of the porphyrin to chlorin Pi-system is necessary for the substrate of BchF hydration. In all the BchF-catalyzed reactions, the products are mixtures of the 31R- and 31S-epimers, and the R-epimers are mainly obtained with a lower amount of the S-epimers. The 20-methylated analogue of Zn-3V[E,M]BPheide d, Zn-3V[E,M]BPheide c, is hydrated by BchF and BchV enzymes to give Zn-[E,M]BPheide c | Chlorobaculum tepidum ATCC 49652 | ? | - |
? | |
| 4.2.1.169 | additional information | in vitro enzymatic hydration of some 3-vinyl-chlorophyll derivatives with usage of zinc complexes of cyclic tetrapyrroles as the enzymatic substrates alternative to chlorophyll(ide)s chelated with magnesium ion. Recombinant BchV catalyzes stereoselective hydration of zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c or d to the zinc 31R-bacteriopheophorbide c or d homologue, respectively, with a slight amount of the 31S-epimeric species. The BchV-hydration gives a relatively larger amount of the 31S-epimers. The in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV. The enzymatic hydration for the 8-propylated substrate proceeds more slowly than that for the 8-ethylated, and the 8-isobutylated substrate is no longer hydrated. The wild-type strain of Chlorobaculum tepidum gives almost exclusively 31R-epimers of 8-ethyl-12-methyl- and 8,12-diethyl-BChl c, approximately 90% 31R- and 10% 31S-epimers of 8-propyl-12-ethyl-BChl c, and entirely 31S-epimer of 8-isobutyl-12-ethyl-BChl c: 4% 31S-epimers in the total amount of BChl c homologues. The in vivo hydrations might be effective even after the 20-methylation by a methyltransferase, BchU. No activity of BchV in the hydration of the 3-vinyl group of protochlorophyllide a, the porphyrin form of chlorophyllide a. The hydrogenation of the porphyrin to chlorin Pi-system is necessary for the substrate of BchV hydration. In all the BchV-catalyzed reactions, the products are mixtures of the 31R- and 31S-epimers, and the R-epimers are mainly obtained with a lower amount of the S-epimers | Chlorobaculum tepidum ATCC 49652 | ? | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O | BchV-hydration gives a relatively larger amount of the 31S epimers | Chlorobaculum tepidum | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O | R-stereoselectivity of BchF | Chlorobaculum tepidum | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O | R-stereoselectivity of BchF | Chlorobaculum tepidum ATCC 49652 | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O | BchV-hydration gives a relatively larger amount of the 31S epimers | Chlorobaculum tepidum ATCC 49652 | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O | BchV-hydration gives a relatively larger amount of the 31S epimers | Chlorobaculum tepidum | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O | R-stereoselectivity of BchF | Chlorobaculum tepidum | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
| 4.2.1.169 | zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O | BchV-hydration gives a relatively larger amount of the 31S epimers | Chlorobaculum tepidum ATCC 49652 | zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 4.2.1.169 | bchF | - |
Chlorobaculum tepidum |
| 4.2.1.169 | BchV | - |
Chlorobaculum tepidum |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 4.2.1.169 | 35 | - |
assay at | Chlorobaculum tepidum |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 4.2.1.169 | 7.8 | - |
assay at | Chlorobaculum tepidum |
Expression
| EC Number | Organism | Comment | Expression |
|---|---|---|---|
| 4.2.1.169 | Chlorobaculum tepidum | the transcriptional level of bchV gene is upregulated under low light conditions | up |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 4.2.1.169 | malfunction | deletion of bchF gene affects the composition of 31R/S-epimers in composite BChls c, the bchF-deleted mutant has nearly 100% R-stereochemistry in 8-ethyl-12-methyl- and 8,12-diethyl-BChls c, 9-12% S-stereochemistry in 8-propyl-12-ethyl-BChl c, and nearly 100% S-stereochemistry in 8-isobutyl-12-ethyl-BChl c | Chlorobaculum tepidum |
| 4.2.1.169 | malfunction | deletion of bchV gene affects the composition of 31R/S-epimers in composite BChls c, the bchV-deleted mutant has nearly 100% R-stereochemistry in 8-ethyl-12-methyl- and 8,12-diethyl-BChls c, 0-6% S-stereochemistry in 8-propyl-12-ethyl-BChl c, and very few 8-isobutyl-12-ethyl-BChl c | Chlorobaculum tepidum |
| 4.2.1.169 | additional information | the central metal is essential for the BchF reaction. Since the 132-methoxycarbonyl group in substrates is not necessary for the enzymatic reactions, the free 172-carboxy group and the central magnesium ion of chlorins are important for the substrates of hydration by BchF enzyme | Chlorobaculum tepidum |
| 4.2.1.169 | additional information | the central metal is essential for the BchV reaction. Since the 132-methoxycarbonyl group in substrates is not necessary for the enzymatic reactions, the free 172-carboxy group and the central magnesium ion of chlorins are important for the substrates of hydration by BchV enzyme | Chlorobaculum tepidum |
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