| Full text | |
| Author(s): |
Kahlert, Lukas
[1]
;
Bernardi, Darlon
[2, 1]
;
Hauser, Maurice
[1]
;
Ioca, Laura P.
[2]
;
Berlinck, Roberto G. S.
[2]
;
Skellam, Elizabeth J.
[1, 3]
;
Cox, Russell J.
[1]
Total Authors: 7
|
| Affiliation: | [1] Leibniz Univ Hannover, Inst Organ Chem & BMWZ, Schneiderberg 38, D-30167 Hannover - Germany
[2] Univ Sao Paulo, Inst Quim Sao Carlos, CP 780, BR-13560970 Sao Carlos, SP - Brazil
[3] Univ North Texas, BioDiscovery Inst, Dept Chem, 1155 Union Circle 305220, Denton, TX 76203 - USA
Total Affiliations: 3
|
| Document type: | Journal article |
| Source: | CHEMISTRY-A EUROPEAN JOURNAL; v. 27, n. 46, p. 11895-11903, AUG 16 2021. |
| Web of Science Citations: | 0 |
| Abstract | |
The mycotoxin terrein is derived from the C-10-precursor 6-hydroxymellein (6-HM) via an oxidative ring contraction. Although the corresponding biosynthetic gene cluster (BGC) has been identified, details of the enzymatic oxidative transformations are lacking. Combining heterologous expression and in vitro studies we show that the flavin-dependent monooxygenase (FMO) TerC catalyzes the initial oxidative decarboxylation of 6-HM. The reactive intermediate is further hydroxylated by the second FMO TerD to yield a highly oxygenated aromatic species, but further reconstitution of the pathway was hampered. A related BGC was identified in the marine-derived Roussoella sp. DLM33 and confirmed by heterologous expression. These studies demonstrate that the biosynthetic pathways of terrein and related (polychlorinated) congeners diverge after oxidative decarboxylation of the lactone precursor that is catalyzed by a conserved FMO and further indicate that early dehydration of the side chain is an essential step. (AU) | |
| FAPESP's process: | 16/05133-7 - Study of marine-derived microrganisms metabolism: chemical profile and biosynthesis |
| Grantee: | Laura Pavan Ióca |
| Support Opportunities: | Scholarships in Brazil - Doctorate |
| FAPESP's process: | 18/10742-8 - The role of a nonribosomal peptide in promoting swarming in Pseudovibrio brasiliensis Ab134 and related bacteria |
| Grantee: | Laura Pavan Ióca |
| Support Opportunities: | Scholarships abroad - Research Internship - Doctorate |
| FAPESP's process: | 16/21341-9 - Hydrophilic and bioactive secondary metabolites produced by filamentous fungi |
| Grantee: | Darlon Irineu Bernardi |
| Support Opportunities: | Scholarships in Brazil - Doctorate (Direct) |
| FAPESP's process: | 13/50228-8 - Biodiversity components, and their metabolic characters, of Brazilian Islands: an integrated approach |
| Grantee: | Roberto Gomes de Souza Berlinck |
| Support Opportunities: | BIOTA-FAPESP Program - Thematic Grants |
| FAPESP's process: | 20/11691-8 - Biosynthesis of roussoellatide, a polyketide isolated from the fungus Roussoella sp. DLM-33 |
| Grantee: | Darlon Irineu Bernardi |
| Support Opportunities: | Scholarships abroad - Research Internship - Doctorate (Direct) |
| FAPESP's process: | 19/17721-9 - The role of Chemistry in holobiont adaptation |
| Grantee: | Roberto Gomes de Souza Berlinck |
| Support Opportunities: | Research Projects - Thematic Grants |