Reaction participants Show >> << Hide
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,799 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ATP Identifier CHEBI:30616 (Beilstein: 3581767) help_outline Charge -4 Formula C10H12N5O13P3 InChIKeyhelp_outline ZKHQWZAMYRWXGA-KQYNXXCUSA-J SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,280 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ilicicolinate B Identifier CHEBI:146152 Charge -1 Formula C23H31O4 InChIKeyhelp_outline QPIZDZGIXDKCRC-JTCWOHKRSA-M SMILEShelp_outline C=1(C(=C(C(=C(C1)C)C(=O)[O-])O)C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,870 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AMP Identifier CHEBI:456215 Charge -2 Formula C10H12N5O7P InChIKeyhelp_outline UDMBCSSLTHHNCD-KQYNXXCUSA-L SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 508 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 ilicicolin B Identifier CHEBI:146153 (CAS: 22581-07-3) help_outline Charge 0 Formula C23H32O3 InChIKeyhelp_outline QAPOXOGEDXIOHD-VZRGJMDUSA-N SMILEShelp_outline C=1(C(=C(C(=C(C1)C)C=O)O)C/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:63080 | RHEA:63081 | RHEA:63082 | RHEA:63083 | |
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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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Biosynthesis of LL-Z1272beta: discovery of a new member of NRPS-like enzymes for aryl-aldehyde formation.
Li C., Matsuda Y., Gao H., Hu D., Yao X.S., Abe I.
LL-Z1272β (1) is a prenylated aryl-aldehyde produced by several fungi; it also serves as a key pathway intermediate for many fungal meroterpenoids. Despite its importance in the biosynthesis of natural products, the molecular basis for the biosynthesis of 1 has yet to be elucidated. Here we identi ... >> More
LL-Z1272β (1) is a prenylated aryl-aldehyde produced by several fungi; it also serves as a key pathway intermediate for many fungal meroterpenoids. Despite its importance in the biosynthesis of natural products, the molecular basis for the biosynthesis of 1 has yet to be elucidated. Here we identified the biosynthetic gene cluster for 1 from Stachybotrys bisbyi PYH05-7, and elucidated the biosynthetic route to 1. The biosynthesis involves a polyketide synthase, a prenyltransferase, and a nonribosomal peptide synthetase (NRPS)-like enzyme, which is responsible for the generation of the aldehyde functionality. Interestingly, the NRPS-like enzyme only accepts the farnesylated substrate to catalyze the carboxylate reduction; this represents a new example of a substrate for adenylation domains. << Less
ChemBioChem 17:904-907(2016) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.
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Complete biosynthetic pathways of ascofuranone and ascochlorin in Acremonium egyptiacum.
Araki Y., Awakawa T., Matsuzaki M., Cho R., Matsuda Y., Hoshino S., Shinohara Y., Yamamoto M., Kido Y., Inaoka D.K., Nagamune K., Ito K., Abe I., Kita K.
Ascofuranone (AF) and ascochlorin (AC) are meroterpenoids produced by various filamentous fungi, including <i>Acremonium egyptiacum</i> (synonym: <i>Acremonium sclerotigenum</i>), and exhibit diverse physiological activities. In particular, AF is a promising drug candidate against African trypanos ... >> More
Ascofuranone (AF) and ascochlorin (AC) are meroterpenoids produced by various filamentous fungi, including <i>Acremonium egyptiacum</i> (synonym: <i>Acremonium sclerotigenum</i>), and exhibit diverse physiological activities. In particular, AF is a promising drug candidate against African trypanosomiasis and a potential anticancer lead compound. These compounds are supposedly biosynthesized through farnesylation of orsellinic acid, but the details have not been established. In this study, we present all of the reactions and responsible genes for AF and AC biosyntheses in <i>A. egyptiacum</i>, identified by heterologous expression, in vitro reconstruction, and gene deletion experiments with the aid of a genome-wide differential expression analysis. Both pathways share the common precursor, ilicicolin A epoxide, which is processed by the membrane-bound terpene cyclase (TPC) AscF in AC biosynthesis. AF biosynthesis branches from the precursor by hydroxylation at C-16 by the P450 monooxygenase AscH, followed by cyclization by a membrane-bound TPC AscI. All genes required for AC biosynthesis (<i>ascABCDEFG</i>) and a transcriptional factor (<i>ascR</i>) form a functional gene cluster, whereas those involved in the late steps of AF biosynthesis (<i>ascHIJ</i>) are present in another distantly located cluster. AF is therefore a rare example of fungal secondary metabolites requiring multilocus biosynthetic clusters, which are likely to be controlled by the single regulator, AscR. Finally, we achieved the selective production of AF in <i>A. egyptiacum</i> by genetically blocking the AC biosynthetic pathway; further manipulation of the strain will lead to the cost-effective mass production required for the clinical use of AF. << Less
Proc. Natl. Acad. Sci. U.S.A. 116:8269-8274(2019) [PubMed] [EuropePMC]
This publication is cited by 9 other entries.