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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Early Oxidative Transformations During the Biosynthesis of Terrein and Related Natural Products

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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; JUN 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: 16/21341-9 - Hydrophilic and bioactive secondary metabolites produced by filamentous fungi
Grantee:Darlon Irineu Bernardi
Support type: Scholarships in Brazil - Doctorate (Direct)
FAPESP's process: 16/05133-7 - Study of marine-derived microrganisms metabolism: chemical profile and biosynthesis
Grantee:Laura Pavan Ióca
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 20/11691-8 - Biosynthesis of roussoellatide, a polyketide isolated from the fungus Roussoella sp. DLM-33
Grantee:Darlon Irineu Bernardi
Support type: Scholarships abroad - Research Internship - 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 type: BIOTA-FAPESP Program - Thematic Grants
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 type: Scholarships abroad - Research Internship - Doctorate
FAPESP's process: 19/17721-9 - The role of Chemistry in holobiont adaptation
Grantee:Roberto Gomes de Souza Berlinck
Support type: Research Projects - Thematic Grants