Collaborative Biosynthesis of Maleimide- and Succinimide-Containing Natural Products by Fungal Polyketide Megasynthases
| Autor: | Jaclyn M. Winter, Leibniz Hang, Michio Sato, Shu-Shan Gao, Neil K. Garg, Yi Tang, Yiu-Sun Hung, Kenji Watanabe, Jacob E. Dander, Man-Cheng Tang, Chizuru Sato |
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| Rok vydání: | 2017 |
| Předmět: |
Stereochemistry
Molecular Conformation Succinimides Peptide 010402 general chemistry 01 natural sciences Biochemistry Article Catalysis Maleimides chemistry.chemical_compound Polyketide Colloid and Surface Chemistry Biosynthesis Succinimide polycyclic compounds Maleimide Adenylylation chemistry.chemical_classification Biological Products 010405 organic chemistry Penicillium General Chemistry 0104 chemical sciences Amino acid chemistry Polyketide Synthases Function (biology) |
| Zdroj: | Journal of the American Chemical Society. 139:5317-5320 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.7b02432 |
| Popis: | Fungal polyketide synthases (PKSs) can function collaboratively to synthesize natural products of significant structural diversity. Here we present a new mode of collaboration between a highly reducing PKS (HRPKS) and a PKS-nonribosomal peptide synthetase (PKS-NRPS) in the synthesis of oxaleimides from the Penicillium species. The HRPKS is recruited in the synthesis of an olefin-containing free amino acid, which is activated and incorporated by the adenylation domain of the PKS-NRPS. The precisely positioned olefin from the unnatural amino acid is proposed to facilitate a scaffold rearrangement of the PKS-NRPS product to forge the maleimide and succinimide cores of oxaleimides. |
| Databáze: | OpenAIRE |
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