Vertirhodins A–F, C-Linked Pyrrolidine-Iminosugar-Containing Pyranonaphthoquinones from Streptomyces sp. B15–008
| Autor: | Carole A. Bewley, Gengxiang Zhao, Jack R. Davison, Robert D. O’Connor, Jiadong Sun |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Magnetic Resonance Spectroscopy
Pyrrolidines Semiquinone Stereochemistry Iminosugar 010402 general chemistry 01 natural sciences Biochemistry Streptomyces Pyrrolidine Article chemistry.chemical_compound Gene cluster Moiety Physical and Theoretical Chemistry Whole genome sequencing Biological Products biology Molecular Structure 010405 organic chemistry Chemistry Circular Dichroism Organic Chemistry Circular dichroism spectra biology.organism_classification 0104 chemical sciences Multigene Family Naphthoquinones |
| Zdroj: | Org Lett |
| Popis: | Six novel pyranonaphthoquinones, vertirhodins A-F (1-6), were discovered from a soil-derived Streptomyces sp. B15-008. Their chemical structures and absolute configurations were determined using nuclear magnetic resonance and comparison of experimental and theoretical electronic circular dichroism spectra. The vertirhodins feature an unusual C-8 N-methyl-2-pyrrolidinemethanol moiety, a 5,14-epoxide rarely seen in streptomyces-derived natural products, and a C-13 hydroxyl group that forms the semiquinone. A plausible ver biosynthetic gene cluster was identified through whole genome sequencing and provides insights into these features. |
| Databáze: | OpenAIRE |
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