4.2.1.165: chlorophyllide a 31-hydratase
This is an abbreviated version!
For detailed information about chlorophyllide a 31-hydratase, go to the full flat file.
Reaction
Synonyms
2-vinyl bacteriochlorophyllide hydratase, 3-vinyl bacteriochlorophyllide a hydratase, 3-vinyl hydratase, 3-vinyl-bacteriochlorophyll hydratase, 31-hydratase, bacterial 3-vinyl hydratase, bchF, BchF hydratase, Cabther_B0080, cfxBchF, ClimR0003, ClimR0008, ClimR0017, craBchF, CT1421
ECTree
4.2.1.165 chlorophyllide a 31-hydrataseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.1.165 - chlorophyllide a 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 a + H2O
3-(1-hydroxyethyl) bacteriochlorophyllide a
-
-
-
r
3-vinyl bacteriochlorophyllide d + H2O
(3R)-(1-hydroxyethyl) bacteriochlorophyllide d + (3S)-(1-hydroxyethyl) bacteriochlorophyllide d
3-vinyl bacteriochlorophyllide d + H2O
(3RS)-3-(1-hydroxyethyl) bacteriochlorophyllide d
low activity, the enzyme converts [E,M], [E,E], [E,P], and [E,I] variants, 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
(31R)-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d
-
-
-
-
?
3-vinyl-8-propyl-12-ethyl-bacteriochlorophyllide d + H2O
(3RS)3-(1-hydroxyethyl)-8-propyl-12-ethyl-bacteriochlorophyllide d
-
-
-
?
3-vinyl-bacteriochlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
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
-
-
?
bacteriochlorophyllide g + H2O
3-(1-hydroxyethyl) bacteriochlorophyllide g
-
-
-
r
chlorophyllide a + H2O
(31R)-3-(1-hydroxyethyl)-chlorophyllide a
-
-
formation of R-enantiomer at the 1-hydroxyethyl group is predominantly synthesized
-
?
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
-
-
?
2-vinyl-bacteriochlorophyllide a + H2O
2-alpha-hydroxyethyl bacteriochlorophyllide a
-
-
-
?
2-vinyl-bacteriochlorophyllide a + H2O
2-alpha-hydroxyethyl bacteriochlorophyllide a
-
-
-
?
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
-
-
-
?
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
-
-
-
-
?
3-deacetyl-3-vinyl-bacteriochlorophyllide a + H2O
3-deacetyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
?
3-deacetyl-3-vinyl-bacteriochlorophyllide a + H2O
3-deacetyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
-
-
-
-
?
3-vinyl bacteriochlorophyllide a + H2O
(31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a
high activity, preferred substrate
-
-
?
3-vinyl bacteriochlorophyllide a + H2O
(31RS)-3-(1-hydroxyethyl) bacteriochlorophyllide a
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
high activity, preferred substrate
-
-
?
3-vinyl bacteriochlorophyllide c + H2O
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide c
-
-
-
?
3-vinyl bacteriochlorophyllide c + H2O
(31RS)3-(1-hydroxyethyl) bacteriochlorophyllide c
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
?
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
(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
(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
(3R)-(1-hydroxyethyl) bacteriochlorophyllide d + (3S)-(1-hydroxyethyl) bacteriochlorophyllide d
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
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
(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-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
-
-
-
?
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
-
-
-
?
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
-
-
-
?
3-vinyl-bacteriochlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
-
-
-
?
3-vinyl-bacteriochlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-bacteriochlorophyllide a
-
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide a
a 3-vinyl bacteriochlorophyllide a + H2O
-
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide a
a 3-vinyl bacteriochlorophyllide a + H2O
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
-
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
a 3-vinyl bacteriochlorophyllide d + H2O
when 3V-bacteriochlorophyllide a is used as a substrate, the enzyme is effective in in vitro hydration
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
a 3-vinyl bacteriochlorophyllide d + H2O
when 3V-bacteriochlorophyllide a is used as a substrate, all enzyme homoluges are effective in in vitro hydration
-
-
?
a 3-(1-hydroxyethyl) bacteriochlorophyllide d
a 3-vinyl bacteriochlorophyllide d + H2O
-
when 3V-bacteriochlorophyllide a is used as a substrate, the enzyme is effective in in vitro hydration
-
-
?
chlorophyllide a + H2O
2-alpha-hydroxyethyl chlorophyllide a
-
-
-
?
chlorophyllide a + H2O
2-alpha-hydroxyethyl chlorophyllide a
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
-
?
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
-
-
-
?
chlorophyllide a + H2O
3-devinyl-3-(1-hydroxyethyl)-chlorophyllide a
-
-
-
-
?
additional information
?
-
in bacteriochlorophyll a biosynthesis, 3-vinyl bacteriochlorophyllide a hydratase BchF converts the 3-hydroxyethyl group on pyrrole ring A into a 3-acetyl group
-
-
?
additional information
?
-
-
in bacteriochlorophyll a biosynthesis, 3-vinyl bacteriochlorophyllide a hydratase BchF converts the 3-hydroxyethyl group on pyrrole ring A into a 3-acetyl group
-
-
?
additional information
?
-
BchF catalyzes the hydration of hypomethylated bacteriochlorophyllide species to produce R-stereochemistry at C-31
-
-
?
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. BchF and BchV can recognize the Pi-conjugated system as their substrate and 17,18-dihydrogenation of porphyrin to chlorin Pi-system is necessary for the substrate of BchF- and BchV-hydration, BchF is active with chlorin and bacteriochlorin in the Pi-conjugate, while BchV is only active with chlorin in the Pi-conjugate, both do not use the porphyrin Pi-conjugate, overview
-
-
?
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. BchF and BchV can recognize the Pi-conjugated system as their substrate and 17,18-dihydrogenation of porphyrin to chlorin Pi-system is necessary for the substrate of BchF- and BchV-hydration, BchF is active with chlorin and bacteriochlorin in the Pi-conjugate, while BchV is only active with chlorin in the Pi-conjugate, both do not use the porphyrin Pi-conjugate, overview
-
-
?
additional information
?
-
coupled enzymatic assays of BchF and BchC are initiated in an anoxic chamber, using either crude cellular BchF and BchC extracts or alternatively a BchF extract and the purified BchC protein, with dithionite as an artificial electron donor (NAD+/NADP+ in in vivo assays), dithiothreitol, ATP, and an ATP-regenerating system (creatine phosphate and creatine phosphokinase) for the analysis of BchC (EC 1.1.1.396) substrate specificity, overview
-
-
?
additional information
?
-
-
coupled enzymatic assays of BchF and BchC are initiated in an anoxic chamber, using either crude cellular BchF and BchC extracts or alternatively a BchF extract and the purified BchC protein, with dithionite as an artificial electron donor (NAD+/NADP+ in in vivo assays), dithiothreitol, ATP, and an ATP-regenerating system (creatine phosphate and creatine phosphokinase) for the analysis of BchC (EC 1.1.1.396) substrate specificity, overview
-
-
?
additional information
?
-
in vitro activity measurements with crude enzyme extract
-
-
?
additional information
?
-
the secondary alcoholic hydroxy group is requisite for chlorosomal aggregation and biosynthesized by hydrating the 3-vinyl group of their precursors through chlorophyllide a 31-hydratase and 3-vinyl bacteriochlorophyllide d 31-hydratase. The enzyme catalyzes stereoselective hydration of zinc 3-vinyl-8-ethyl-12-methyl-bacteriopheophorbide c to the zinc (31R)-bacteriopheophorbide c homologue, with a slight amount of the (31S)-epimeric species. R-stereoselectivity is observed in the BchF-hydration of zinc 3-vinyl-8-ethyl-12-ethyl-bacteriopheophorbides c. The wild-type strain gives almost exclusively (31R)-epimers of 8-ethyl-12-methyl-(R[E,M]BChl c) and 8,12-diethyl-BChl c (R[E,E]BChl c), approximately 90% (31R)- and 10% (31S)-epimers of 8-propyl-12-ethyl-BChl c (R[P,E]BChl c and S[P,E]BChl c), and entirely 31S-epimer of 8-isobutyl-12-ethyl-BChl c (S[I,E]BChl c), 4% 31S-epimers in the total amount of BChl c homologues
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
coupled enzymatic assays of BchF and BchC are initiated in an anoxic chamber, using either crude cellular BchF and BchC extracts or alternatively a BchF extract and the purified BchC protein, with dithionite as an artificial electron donor (NAD+/NADP+ in in vivo assays), dithiothreitol, ATP, and an ATP-regenerating system (creatine phosphate and creatine phosphokinase) for the analysis of BchC (EC 1.1.1.396) substrate specificity, overview
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
in vitro activity measurements with crude enzyme extract
-
-
?
additional information
?
-
Chlorobaculum tepidum ATCC 49652 / DSM 12025 / NBRC 103806 / TLS
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. BchF and BchV can recognize the Pi-conjugated system as their substrate and 17,18-dihydrogenation of porphyrin to chlorin Pi-system is necessary for the substrate of BchF- and BchV-hydration, BchF is active with chlorin and bacteriochlorin in the Pi-conjugate, while BchV is only active with chlorin in the Pi-conjugate, both do not use the porphyrin Pi-conjugate, overview
-
-
?
additional information
?
-
in bacteriochlorophyll a biosynthesis, 3-vinyl bacteriochlorophyllide a hydratase BchF converts the 3-hydroxyethyl group on pyrrole ring A into a 3-acetyl group
-
-
?
additional information
?
-
BchF catalyzes the hydration of hypomethylated bacteriochlorophyllide species to produce R-stereochemistry at C-31
-
-
?
additional information
?
-
-
the enzyme BchF produces an approximately 9:1 mixture of 31R- and S-epimers of the product
-
-
?
