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12-epi-fischerindole U + 2-oxoglutarate + O2 + bromide
13R-bromo-12-epi-fischerindole U + succinate + CO2 + H2O
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
ambiguine C + 2-oxoglutarate + O2 + chloride
ambiguine B + succinate + CO2 + H2O
ambiguine H + 2-oxoglutarate + O2 + chloride
ambiguine A + succinate + CO2 + H2O
ambiguine I + 2-oxoglutarate + O2 + chloride
ambiguine E + succinate + CO2 + H2O
ambiguine L + 2-oxoglutarate + O2 + chloride
ambiguine K + succinate + CO2 + H2O
hapalindole U + 2-oxoglutarate + O2 + chloride
hapalindole G + succinate + CO2 + H2O
additional information
?
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12-epi-fischerindole U + 2-oxoglutarate + O2 + bromide
13R-bromo-12-epi-fischerindole U + succinate + CO2 + H2O
pre-saturating the WelO5 active site with a non-native bromide anion is found to be critical to the highly selective in vitro transfer of bromine, instead of chlorine
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12-epi-fischerindole U + 2-oxoglutarate + O2 + bromide
13R-bromo-12-epi-fischerindole U + succinate + CO2 + H2O
pre-saturating the WelO5 active site with a non-native bromide anion is found to be critical to the highly selective in vitro transfer of bromine, instead of chlorine
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12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
the rate of conversion of 12-epi-hapalindole C to 12-epi-hapalindole E by WelO5 is less than that for conversion of 12-epi-fischerindole U to 12-epi-fischerindole G. 12-epi-fischerindole U is the preferred substrate
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-
?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epi-fischerindole U as WelO5
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-
?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epifischerindole U as WelO5
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-
?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epi-fischerindole U as WelO5
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12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epifischerindole U as WelO5
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
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?
12-epi-fischerindole U + 2-oxoglutarate + O2 + chloride
12-epi-fischerindole G + succinate + CO2 + H2O
the rate of conversion of 12-epi-hapalindole C to 12-epi-hapalindole E by WelO5 is less than that for conversion of 12-epi-fischerindole U to 12-epi-fischerindole G. 12-epi-fischerindole U is the preferred substrate
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
the rate of conversion of 12-epi-hapalindole C to 12-epi-hapalindole E by WelO5 is less than that for conversion of 12-epi-fischerindole U to 12-epi-fischerindole G. 12-epi-fischerindole U is the preferred substrate
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?
12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epi-fischerindole U as WelO5
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epifischerindole U as WelO5
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epi-fischerindole U as WelO5
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
WelO5* from Hapalosiphon welwitschii IC-52-3 exhibits an enhanced specificity towards 12-epi-hapalindole C, a substrate poorly processed by WelO5 from Hapalosiphon welwitschii UTEX B1830, while maintaining its fidelity towards 12-epifischerindole U as WelO5
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
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12-epi-hapalindole C + 2-oxoglutarate + O2 + chloride
12-epi-hapalindole E + succinate + CO2 + H2O
the rate of conversion of 12-epi-hapalindole C to 12-epi-hapalindole E by WelO5 is less than that for conversion of 12-epi-fischerindole U to 12-epi-fischerindole G. 12-epi-fischerindole U is the preferred substrate
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?
ambiguine C + 2-oxoglutarate + O2 + chloride
ambiguine B + succinate + CO2 + H2O
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ambiguine C + 2-oxoglutarate + O2 + chloride
ambiguine B + succinate + CO2 + H2O
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ambiguine C + 2-oxoglutarate + O2 + chloride
ambiguine B + succinate + CO2 + H2O
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ambiguine H + 2-oxoglutarate + O2 + chloride
ambiguine A + succinate + CO2 + H2O
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ambiguine H + 2-oxoglutarate + O2 + chloride
ambiguine A + succinate + CO2 + H2O
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ambiguine H + 2-oxoglutarate + O2 + chloride
ambiguine A + succinate + CO2 + H2O
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ambiguine I + 2-oxoglutarate + O2 + chloride
ambiguine E + succinate + CO2 + H2O
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ambiguine I + 2-oxoglutarate + O2 + chloride
ambiguine E + succinate + CO2 + H2O
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ambiguine I + 2-oxoglutarate + O2 + chloride
ambiguine E + succinate + CO2 + H2O
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?
ambiguine L + 2-oxoglutarate + O2 + chloride
ambiguine K + succinate + CO2 + H2O
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ambiguine L + 2-oxoglutarate + O2 + chloride
ambiguine K + succinate + CO2 + H2O
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?
hapalindole U + 2-oxoglutarate + O2 + chloride
hapalindole G + succinate + CO2 + H2O
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hapalindole U + 2-oxoglutarate + O2 + chloride
hapalindole G + succinate + CO2 + H2O
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additional information
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no activity with hapalindole U, ambiguine H, ambiguine C, ambiguine L, ambiguine I, ambiguine E
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additional information
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no activity with hapalindole U, ambiguine H, ambiguine C, ambiguine L, ambiguine I, ambiguine E
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G166D
2.5 A resolution structure of G166D WelO5 in complex with 12-epi-fischerindole U shows that Asp166 coordinates FeII and the substrate location observed in wilde-type enzyme WelO5 is retained in the variant enzyme
H259F
mutant enzyme lacks chlorination activity on 12-epi-fischerindole U
G166D
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2.5 A resolution structure of G166D WelO5 in complex with 12-epi-fischerindole U shows that Asp166 coordinates FeII and the substrate location observed in wilde-type enzyme WelO5 is retained in the variant enzyme
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H259F
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mutant enzyme lacks chlorination activity on 12-epi-fischerindole U
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additional information
generation of a pair of chimeric proteins by fusing the N-terminal WelO5 (aa1-145) from Hapalosiphon welwitschii UTEX B 1830 with C-terminal AmbO5 (aa146-290) from Fischerella ambigua to give WelO5AmbO5 and vice versa to give AmbO5WelO5. WelO5AmbO5 is able to convert ambiguine C to ambiguine B, albeit at a lower efficiency comparing with wild-type AmbO5, whereas AmbO5WelO5 shows no measurable activity towards ambiguine C under identical assay conditions. This result implicates the C-terminal residues of AmbO5 may play a role on its broadened substrate scope
additional information
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a WelO5-variant is constructed by swapping the residues 215-232 of WelO5 from Hapalosiphon welwitschii UTEX B1830 to those of WelO5* of Hapalosiphon welwitschii IC-52-3. The variant displays a noticeably enhanced activity towards 12-epi-hapalindole C. The activity of WelO5-var towards 12-epi-hapalindole C is elevated to a comparable level as the wild type WelO5* from Hapalosiphon welwitschii IC-52-3, while retaining its fidelity towards 12-epi-fischerindole U
additional information
a WelO5-variant is constructed by swapping the residues 215-232 of WelO5 from Hapalosiphon welwitschii UTEX B1830 to those of WelO5* of Hapalosiphon welwitschii IC-52-3. The variant displays a noticeably enhanced activity towards 12-epi-hapalindole C. The activity of WelO5-var towards 12-epi-hapalindole C is elevated to a comparable level as the wild type WelO5* from Hapalosiphon welwitschii IC-52-3, while retaining its fidelity towards 12-epi-fischerindole U
additional information
generation of a pair of chimeric proteins by fusing the N-terminal WelO5 (aa1-145) from Hapalosiphon welwitschii UTEX B 1830 with C-terminal AmbO5 (aa146-290) from Fischerella ambigua to give WelO5AmbO5 and vice versa to give AmbO5WelO5. WelO5AmbO5 is able to convert ambiguine C to ambiguine B, albeit at a lower efficiency comparing with wild-type AmbO5, whereas AmbO5WelO5 shows no measurable activity towards ambiguine C under identical assay conditions. This result implicates the C-terminal residues of AmbO5 may play a role on its broadened substrate scope
additional information
-
a WelO5-variant is constructed by swapping the residues 215-232 of WelO5 from Hapalosiphon welwitschii UTEX B1830 to those of WelO5* of Hapalosiphon welwitschii IC-52-3. The variant displays a noticeably enhanced activity towards 12-epi-hapalindole C. The activity of WelO5-var towards 12-epi-hapalindole C is elevated to a comparable level as the wild type WelO5* from Hapalosiphon welwitschii IC-52-3, while retaining its fidelity towards 12-epi-fischerindole U
-
additional information
-
generation of a pair of chimeric proteins by fusing the N-terminal WelO5 (aa1-145) from Hapalosiphon welwitschii UTEX B 1830 with C-terminal AmbO5 (aa146-290) from Fischerella ambigua to give WelO5AmbO5 and vice versa to give AmbO5WelO5. WelO5AmbO5 is able to convert ambiguine C to ambiguine B, albeit at a lower efficiency comparing with wild-type AmbO5, whereas AmbO5WelO5 shows no measurable activity towards ambiguine C under identical assay conditions. This result implicates the C-terminal residues of AmbO5 may play a role on its broadened substrate scope
-
additional information
-
a WelO5-variant is constructed by swapping the residues 215-232 of WelO5 from Hapalosiphon welwitschii UTEX B1830 to those of WelO5* of Hapalosiphon welwitschii IC-52-3. The variant displays a noticeably enhanced activity towards 12-epi-hapalindole C. The activity of WelO5-var towards 12-epi-hapalindole C is elevated to a comparable level as the wild type WelO5* from Hapalosiphon welwitschii IC-52-3, while retaining its fidelity towards 12-epi-fischerindole U
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Hillwig, M.L.; Zhu, Q.; Ittiamornkul, K.; Liu, X.
Discovery of a promiscuous non-heme iron halogenase in ambiguine alkaloid biogenesis implication for an evolvable enzyme family for late-stage halogenation of aliphatic carbons in small molecules
Angew. Chem. Int. Ed. Engl.
55
5780-5784
2016
Fischerella ambigua (A0A076NA91), Hapalosiphon welwitschii (A0A067YX61), Hapalosiphon welwitschii UTEX B 1830 (A0A067YX61)
brenda
Zhu, Q.; Liu, X.
Characterization of non-heme iron aliphatic halogenase WelO5* from Hapalosiphon welwitschii IC-52-3 Identification of a minimal protein sequence motif that confers enzymatic chlorination specificity in the biosynthesis
Beilstein J. Org. Chem.
13
1168-1173
2017
Hapalosiphon welwitschii, Hapalosiphon welwitschii (A0A067YX61), Hapalosiphon welwitschii UTEX B 1830 (A0A067YX61), Hapalosiphon welwitschii IC-52-3
brenda
Zhu, Q.; Hillwig, M.L.; Doi, Y.; Liu, X.
Aliphatic halogenase enables late-stage C-H functionalization selective synthesis of a brominated Fischerindole alkaloid with enhanced antibacterial activity
ChemBioChem
17
466-470
2016
Hapalosiphon welwitschii (A0A067YX61), Hapalosiphon welwitschii UTEX B 1830 (A0A067YX61)
brenda
Liu, X.
In vitro analysis of cyanobacterial nonheme iron-dependent aliphatic halogenases WelO5 and AmbO5
Methods Enzymol.
604
389-404
2018
Hapalosiphon welwitschii (A0A067YX61), Fischerella ambigua (A0A1L1YPD7), Fischerella ambigua UTEX 1903 (A0A1L1YPD7), Hapalosiphon welwitschii UTEX B 1830 (A0A067YX61)
brenda
Hillwig, M.L.; Liu, X.
A new family of iron-dependent halogenases acts on freestanding substrates
Nat. Chem. Biol.
10
921-923
2014
Hapalosiphon welwitschii (A0A067YX61), Hapalosiphon welwitschii UTEX B 1830 (A0A067YX61)
brenda
Mitchell, A.J.; Zhu, Q.; Maggiolo, A.O.; Ananth, N.R.; Hillwig, M.L.; Liu, X.; Boal, A.K.
Structural basis for halogenation by iron- and 2-oxo-glutarate-dependent enzyme WelO5
Nat. Chem. Biol.
12
636-640
2016
Hapalosiphon welwitschii (A0A067YX61), Hapalosiphon welwitschii UTEX B 1830 (A0A067YX61)
brenda