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- Name help_outline (+)-malbrancheamide B Identifier CHEBI:145677 Charge 1 Formula C21H25ClN3O InChIKeyhelp_outline DXPVAKSJZFQGSS-DQLDELGASA-O SMILEShelp_outline C1=C2C(=CC=C1Cl)C3=C(N2)C([C@]4([C@@]5(C3)C[NH+]6[C@](C4)(CCC6)C(N5)=O)[H])(C)C 2D coordinates Mol file for the small molecule Search links Involved in 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline bromide Identifier CHEBI:15858 (Beilstein: 3587179; CAS: 24959-67-9) help_outline Charge -1 Formula Br InChIKeyhelp_outline CPELXLSAUQHCOX-UHFFFAOYSA-M SMILEShelp_outline [Br-] 2D coordinates Mol file for the small molecule Search links Involved in 24 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline FAD Identifier CHEBI:57692 Charge -3 Formula C27H30N9O15P2 InChIKeyhelp_outline IMGVNJNCCGXBHD-UYBVJOGSSA-K SMILEShelp_outline Cc1cc2nc3c(nc(=O)[n-]c3=O)n(C[C@H](O)[C@H](O)[C@H](O)COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n3cnc4c(N)ncnc34)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 170 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (+)-malbrancheamide D Identifier CHEBI:145929 Charge 1 Formula C21H24BrClN3O InChIKeyhelp_outline VLIVGPAAISBPTR-DQLDELGASA-O SMILEShelp_outline C1=C2C(=CC(=C1Cl)Br)C3=C(N2)C([C@]4([C@@]5(C3)C[NH+]6[C@](C4)(CCC6)C(N5)=O)[H])(C)C 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline FADH2 Identifier CHEBI:58307 Charge -2 Formula C27H33N9O15P2 InChIKeyhelp_outline YPZRHBJKEMOYQH-UYBVJOGSSA-L SMILEShelp_outline Cc1cc2Nc3c([nH]c(=O)[nH]c3=O)N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)n3cnc4c(N)ncnc34)c2cc1C 2D coordinates Mol file for the small molecule Search links Involved in 161 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:62728 | RHEA:62729 | RHEA:62730 | RHEA:62731 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Function and structure of MalA/MalA', iterative halogenases for late-stage C-H functionalization of indole alkaloids.
Fraley A.E., Garcia-Borras M., Tripathi A., Khare D., Mercado-Marin E.V., Tran H., Dan Q., Webb G.P., Watts K.R., Crews P., Sarpong R., Williams R.M., Smith J.L., Houk K.N., Sherman D.H.
Malbrancheamide is a dichlorinated fungal indole alkaloid isolated from both Malbranchea aurantiaca and Malbranchea graminicola that belongs to a family of natural products containing a characteristic bicyclo[2.2.2]diazaoctane core. The introduction of chlorine atoms on the indole ring of malbranc ... >> More
Malbrancheamide is a dichlorinated fungal indole alkaloid isolated from both Malbranchea aurantiaca and Malbranchea graminicola that belongs to a family of natural products containing a characteristic bicyclo[2.2.2]diazaoctane core. The introduction of chlorine atoms on the indole ring of malbrancheamide differentiates it from other members of this family and contributes significantly to its biological activity. In this study, we characterized the two flavin-dependent halogenases involved in the late-stage halogenation of malbrancheamide in two different fungal strains. MalA and MalA' catalyze the iterative dichlorination and monobromination of the free substrate premalbrancheamide as the final steps in the malbrancheamide biosynthetic pathway. Two unnatural bromo-chloro-malbrancheamide analogues were generated through MalA-mediated chemoenzymatic synthesis. Structural analysis and computational studies of MalA' in complex with three substrates revealed that the enzyme represents a new class of zinc-binding flavin-dependent halogenases and provides new insights into a potentially unique reaction mechanism. << Less
J. Am. Chem. Soc. 139:12060-12068(2017) [PubMed] [EuropePMC]
This publication is cited by 8 other entries.