The readily available and enzymatically derived cis-1,2-dihydrocatechol 3 has been converted, over 15 steps, into (+)-amabiline, the non-natural enantiomeric form of a crinine-type alkaloid.
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http://dx.doi.org/10.1021/ol901230w | DOI Listing |
Angew Chem Int Ed Engl
December 2024
TU Dresden: Technische Universitat Dresden, Faculty of Chemistry and Food Chemistry, Bergstraße 66, 01069, Dresden, GERMANY.
Polycyclic tetramate macrolactams (PoTeMs) represent a growing class of bioactive natural products that are derived from a common tetramate polyene precursor, lysobacterene A, produced by an unusual bacterial iterative polyketide synthase (PKS) / non-ribosomal peptide synthetase (NRPS). The structural and functional diversity of PoTeMs is biosynthetically elaborated from lysobacterene A by pathway-specific cyclizing and modifying enzymes. This results in diverse core structure decoration and cyclization patterns.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Fudan University, School of Pharmacy, CHINA.
Drimane-type merosesquiterpenoids (DMT) are a class of natural products with diverse structures and broad biological activity. Classical DMT synthesis relies on atom-inefficient plant-derived chiral pool building blocks, while alternative drimane-type building blocks such as drimenol and albicanol offer more direct routes but face production challenges. In this study, we engineered a microbial platform for efficient production of these building blocks.
View Article and Find Full Text PDFMolecules
December 2024
Science Institute, Chemistry Department, University of Iceland, Dunhaga 3, 107 Reykjavik, Iceland.
This report describes the asymmetric synthesis of a focused library of enantiopure structured triacylglycerols (TAGs) comprised of a single saturated fatty acid (C6, C8, C10, C12, C14 or C16), a pure bioactive n-3 polyunsaturated fatty acid (EPA or DHA) and a potent drug (ibuprofen or naproxen) intended as a novel type of prodrug. One of the terminal -1 or -3 positions of the glycerol backbone is occupied with a saturated fatty, the remaining one with a PUFA, and the drug entity is present in the -2 position. This was accomplished by a six-step chemoenzymatic approach starting from enantiopure ()- and ()-solketals.
View Article and Find Full Text PDFOrg Lett
November 2024
The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
Org Lett
November 2024
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, Georgia 30332, United States.
The chemical synthesis of -acyl indoles is hindered by the poor nucleophilicity of indolic nitrogen, necessitating the use of strongly basic reaction conditions that encumber elaboration of highly functionalized scaffolds. Herein, we describe the total chemoenzymatic synthesis of the bulbiferamide natural products by the biochemical activity reconstitution of a nonribosomal peptide synthetase assembly line-derived (NRPS-derived) thioesterase that neatly installs the macrocyclizing indolylamide. The enzyme represents a starting point for biocatalytic access to macrocyclic indolylamide peptides and natural products.
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