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- Name help_outline 6-hydroxydeoxybrevianamide E Identifier CHEBI:145682 Charge 0 Formula C21H25N3O3 InChIKeyhelp_outline DHOZDQLRUFUUQZ-IRXDYDNUSA-N SMILEShelp_outline N12C([C@@H](NC([C@@]1(CCC2)[H])=O)CC3=C(NC4=C3C=CC(=C4)O)C(C=C)(C)C)=O 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 dimethylallyl diphosphate Identifier CHEBI:57623 (Beilstein: 5288443; CAS: 22679-02-3) help_outline Charge -3 Formula C5H9O7P2 InChIKeyhelp_outline CBIDRCWHNCKSTO-UHFFFAOYSA-K SMILEShelp_outline CC(C)=CCOP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 79 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,129 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline notoamide S Identifier CHEBI:145683 Charge 0 Formula C26H33N3O3 InChIKeyhelp_outline ZGWIWQJHQKPWGB-PMACEKPBSA-N SMILEShelp_outline N12C([C@@H](NC([C@@]1(CCC2)[H])=O)CC3=C(NC4=C3C=CC(=C4CC=C(C)C)O)C(C=C)(C)C)=O 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
Cross-references
| RHEA:62344 | RHEA:62345 | RHEA:62346 | RHEA:62347 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp.
Ding Y., de Wet J.R., Cavalcoli J., Li S., Greshock T.J., Miller K.A., Finefield J.M., Sunderhaus J.D., McAfoos T.J., Tsukamoto S., Williams R.M., Sherman D.H.
Stephacidin and notoamide natural products belong to a group of prenylated indole alkaloids containing a core bicyclo[2.2.2]diazaoctane ring system. These bioactive fungal secondary metabolites have a range of unusual structural and stereochemical features but their biosynthesis has remained uncha ... >> More
Stephacidin and notoamide natural products belong to a group of prenylated indole alkaloids containing a core bicyclo[2.2.2]diazaoctane ring system. These bioactive fungal secondary metabolites have a range of unusual structural and stereochemical features but their biosynthesis has remained uncharacterized. Herein, we report the first biosynthetic gene cluster for this class of fungal alkaloids based on whole genome sequencing of a marine-derived Aspergillus sp. Two central pathway enzymes catalyzing both normal and reverse prenyltransfer reactions were characterized in detail. Our results establish the early steps for creation of the prenylated indole alkaloid structure and suggest a scheme for the biosynthesis of stephacidin and notoamide metabolites. The work provides the first genetic and biochemical insights for understanding the structural diversity of this important family of fungal alkaloids. << Less
J. Am. Chem. Soc. 132:12733-12740(2010) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.