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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Bibliographic Details
Published inOrganic letters Vol. 26; no. 17; pp. 3597 - 3601
Main Authors Chen, Lin, Wang, Xin, Zou, Yi, Tang, Man-Cheng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.05.2024
Amer Chemical Soc
Subjects
Amino Acids - chemistry
Amino Acids - metabolism
Arabidopsis
Chemistry
Chemistry, Organic
Leucine - chemistry
Leucine - metabolism
Molecular Structure
Peptide Synthases - genetics
Peptide Synthases - metabolism
Physical Sciences
Plant Roots
Polyketide Synthases - metabolism
Science & Technology
PERCEPTION
BIOSYNTHESIS
OCHRATOXIN
DIVERSITY
IDENTIFICATION
METABOLITE
PSEUROTIN
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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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c01039