4.2.1.169: 3-vinyl bacteriochlorophyllide d 31-hydratase
This is an abbreviated version!
For detailed information about 3-vinyl bacteriochlorophyllide d 31-hydratase, go to the full flat file.
Reaction
Synonyms
3-vinyl hydratase, bacterial 3-vinyl hydratase, bacteriochlorophyll c3(1) hydratase, bchF, BchV, C3-vinyl hydratase, chV, CT1776
ECTree
4.2.1.169 3-vinyl bacteriochlorophyllide d 31-hydrataseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 4.2.1.169 - 3-vinyl bacteriochlorophyllide d 31-hydratase
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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
3-deacetyl-3-vinyl-bacteriochlorophyllide a + H2O
3-deacetyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
3-vinyl bacteriochlorophyllide d + H2O
(3R)-(1-hydroxyethyl) bacteriochlorophyllide d + (3S)-(1-hydroxyethyl) bacteriochlorophyllide d
-
reaction mixture of Zn-3V-[E,M] or Zn-3V-[E,E]/[P,E]/[I,E]bacteriopheophorbide d homologues, overview
-
-
?
3-vinyl bacteriochlorophyllide d + H2O
(3RS)-3-(1-hydroxyethyl) bacteriochlorophyllide d
-
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
-
-
?
3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d
3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d
3-vinyl-8-isobutyl-12-ethyl-bacteriochlorophyllide d + H2O
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide d
-
-
-
-
?
3-vinyl-8-propyl-12-ethyl-bacteriochlorophyllide d + H2O
(3RS)3-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d
-
-
-
-
?
8-methylated 3-vinyl bacteriochlorophyllide d + H2O
?
-
the enzyme forms Zn-R[P,E]bacteriopheophorbide d as a major product and Zn-S[P,E]bacteriopheophorbide d as a minor one
-
-
?
zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide d + H2O
zinc (31R)-8-ethyl-12-methyl-bacteriopheophorbide d + zinc (31S)-8-ethyl-12-methyl-bacteriopheophorbide d
-
-
-
-
?
zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
12-methylated 3-vinyl bacteriochlorophyllide d + H2O
?
-
the enzyme forms a 31-epimeric mixture of Zn-R/S[E,E]bacteriopheophorbide d
-
-
?
12-methylated 3-vinyl bacteriochlorophyllide d + H2O
?
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
the enzyme forms a 31-epimeric mixture of Zn-R/S[E,E]bacteriopheophorbide d
-
-
?
3-deacetyl-3-vinyl-bacteriochlorophyllide a + H2O
3-deacetyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
-
-
-
-
?
3-deacetyl-3-vinyl-bacteriochlorophyllide a + H2O
3-deacetyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
-
?
3-vinyl bacteriochlorophyllide a + H2O
(31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a
-
-
-
-
?
3-vinyl bacteriochlorophyllide a + H2O
(31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
-
?
3-vinyl bacteriochlorophyllide c + H2O
(31S)-3-(1-hydroxyethyl) bacteriochlorophyllide c
-
low activity
-
-
?
3-vinyl bacteriochlorophyllide c + H2O
(31S)-3-(1-hydroxyethyl) bacteriochlorophyllide c
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
low activity
-
-
?
3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d
-
-
-
-
?
3-vinyl-8,12-diethyl-bacteriochlorophyllide d + H2O
(31R)-(1-hydroxyethyl)-8,12-diethyl-bacteriochlorophyllide d
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
-
?
3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d
-
-
-
-
?
3-vinyl-8-ethyl-12-methyl-bacteriochlorophyllide d + H2O
(31R)-(1-hydroxyethyl)-8-ethyl-12-methyl-bacteriochlorophyllide d
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
a 3-vinyl bacteriochlorophyllide d + H2O
-
-
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
a 3-vinyl bacteriochlorophyllide d + H2O
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
-
?
a 3-vinyl bacteriochlorophyllide a + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide a
-
-
-
?
a 3-vinyl bacteriochlorophyllide a + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide a
enzyme BchV prefers the S-stereoisomer, stereospecific reaction
-
-
?
a 3-vinyl bacteriochlorophyllide a + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide a
-
-
-
?
a 3-vinyl bacteriochlorophyllide a + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide a
enzyme BchV prefers the S-stereoisomer, stereospecific reaction
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
-
-
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
-
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
-
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
bacteriochlorophyllide d is converted to bacteriochlorophyllide c
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
enzyme BchV prefers the S-stereoisomer, stereospecific reaction
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
enzyme BchV prefers the S-stereoisomer, stereospecific reaction
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
Chlorobaculum tepidum ATCC 49652
-
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
Chlorobaculum tepidum ATCC 49652
enzyme BchV prefers the S-stereoisomer, stereospecific reaction
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
-
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
bacteriochlorophyllide d is converted to bacteriochlorophyllide c
-
-
?
a 3-vinyl bacteriochlorophyllide d + H2O
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
enzyme BchV prefers the S-stereoisomer, stereospecific reaction
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
cf. EC 4.2.1.165
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
cf. EC 4.2.1.165
-
-
?
zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
BchV-hydration gives a relatively larger amount of the 31S epimers
-
-
?
zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
R-stereoselectivity of BchF
-
-
?
zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
Chlorobaculum tepidum ATCC 49652
R-stereoselectivity of BchF
-
-
?
zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
Chlorobaculum tepidum ATCC 49652
BchV-hydration gives a relatively larger amount of the 31S epimers
-
-
?
zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
BchV-hydration gives a relatively larger amount of the 31S epimers
-
-
?
zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
R-stereoselectivity of BchF
-
-
?
zinc 3-vinyl-8-propyl-12-methyl-bacteriopheophorbide c + H2O
zinc 31R-bacteriopheophorbide c + zinc 31S-bacteriopheophorbide c
Chlorobaculum tepidum ATCC 49652
BchV-hydration gives a relatively larger amount of the 31S epimers
-
-
?
additional information
?
-
the enzyme is a bacteriochlorophyllide c-specific BchF paralogue, cf. EC 4.2.1.165. BchV catalyzes the hydration of the C-3 vinyl group of highly methylated bacteriochlorophyllide species to produce S-stereochemistry
-
-
?
additional information
?
-
-
the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV
-
-
?
additional information
?
-
the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV
-
-
?
additional information
?
-
the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
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
-
-
?
additional information
?
-
-
both BchF and BchV from Chlorobaculum tepidum catalyze in vitro hydration of the 3-vinyl group of Zn-3V-[E,M]bacteriopheophorbide d. The reaction of Zn-3V-[E,E]bacteriopheophorbide d, the 121-methylated derivative of Zn-3V-[E,M]bacteriopheophorbides d, shows two products assigned to a 31-epimeric mixture of Zn-R/S[E,E]bacteriopheophorbide d. The R-epimeric product is predominant. Zn-3V-[P,E]bacteriopheophorbide d, the homologue methylated at the 82-position of Zn-3V-[E,E]bacteriopheophorbide d as a substrate gives similar results to that of Zn-3V-[E,E]bacteriopheophorbide d. Both BchF and BchV hydrate Zn-3V-[P,E]bacteriopheophorbide d stereoselectively and produce Zn-R[P,E]bacteriopheophorbide d as a major product and Zn-S[P,E]bacteriopheophorbide d as a minor one. With one more 82-methylated pigment, Zn-3V-[I,E]bacteriopheophorbide d, both BchF and BchV hydrate the 3-vinyl group of the substrate. No activity of BchF or BchV with Zn-3V-[I,E]bacteriopheophorbide c, the 20-methylated derivative of Zn-3V-[I,E]bacteriopheophorbide d
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-
?
additional information
?
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-
in vitro activity measurements with crude enzyme extract
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-
?
additional information
?
-
-
the enzyme catalyzes stereoselective hydration of zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide d to the zinc 31R-bacteriopheophorbide d homologue with a slight amount of the 31S-epimric species. BchV-hydration of zinc 3-vinyl-8-ethyl and propyl-12-ethyl-bacteriopheophorbides c gives a relatively larger amount of the 31S-epimers. Stereoselectivity is observed in the BchF-hydration of zinc 3-vinyl-8-propyl-12-ethyl-bacteriopheophorbides c resulting in a relatively larger amount of the 31S-epimers
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652
the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652
the in vitro stereoselective hydration confirms the in vivo production of the S-epimeric species by BchV
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652
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
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652
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
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-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652
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
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-
?
additional information
?
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Chlorobaculum tepidum ATCC 49652
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
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Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
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in vitro activity measurements with crude enzyme extract
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additional information
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Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
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both BchF and BchV from Chlorobaculum tepidum catalyze in vitro hydration of the 3-vinyl group of Zn-3V-[E,M]bacteriopheophorbide d. The reaction of Zn-3V-[E,E]bacteriopheophorbide d, the 121-methylated derivative of Zn-3V-[E,M]bacteriopheophorbides d, shows two products assigned to a 31-epimeric mixture of Zn-R/S[E,E]bacteriopheophorbide d. The R-epimeric product is predominant. Zn-3V-[P,E]bacteriopheophorbide d, the homologue methylated at the 82-position of Zn-3V-[E,E]bacteriopheophorbide d as a substrate gives similar results to that of Zn-3V-[E,E]bacteriopheophorbide d. Both BchF and BchV hydrate Zn-3V-[P,E]bacteriopheophorbide d stereoselectively and produce Zn-R[P,E]bacteriopheophorbide d as a major product and Zn-S[P,E]bacteriopheophorbide d as a minor one. With one more 82-methylated pigment, Zn-3V-[I,E]bacteriopheophorbide d, both BchF and BchV hydrate the 3-vinyl group of the substrate. No activity of BchF or BchV with Zn-3V-[I,E]bacteriopheophorbide c, the 20-methylated derivative of Zn-3V-[I,E]bacteriopheophorbide d
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the enzyme is a bacteriochlorophyllide c-specific BchF paralogue, cf. EC 4.2.1.165. BchV catalyzes the hydration of the C-3 vinyl group of highly methylated bacteriochlorophyllide species to produce S-stereochemistry
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