Genome Mining of a Fungal Polyketide Synthase–Nonribosomal Peptide Synthetase Hybrid Megasynthetase Pathway to Synthesize a Phytotoxic N‑Acyl Amino Acid
Guided by the retrobiosynthesis hypothesis, we characterized a fungal polyketide synthase–nonribosomal peptide synthetase (PKS–NRPS) hybrid megasynthetase pathway to generate 2-trans-4-trans-2-methylsorbyl-d-leucine (1), a polyketide amino acid conjugate that inhibits Arabidopsis root growth. The bi...
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Published in | Organic letters Vol. 26; no. 17; pp. 3597 - 3601 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
03.05.2024
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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Summary: | Guided by the retrobiosynthesis hypothesis, we characterized a fungal polyketide synthase–nonribosomal peptide synthetase (PKS–NRPS) hybrid megasynthetase pathway to generate 2-trans-4-trans-2-methylsorbyl-d-leucine (1), a polyketide amino acid conjugate that inhibits Arabidopsis root growth. The biosynthesis of 1 includes a PKS–NRPS enzyme to assemble an N-acyl amino alcohol intermediate, which is further oxidized to an N-acyl amino acid (NAAA), demonstrating a new biosynthetic logic for synthesizing NAAAs and expanding the chemical space of products encoded by fungal PKS–NRPS clusters. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.4c01039 |