Structure and biosynthesis of sorangipyranone - a new γ-dihydropyrone from the myxobacterial strain MSr12020.
Average rating
Cast your vote
You can rate an item by clicking the amount of stars they wish to award to this item.
When enough users have cast their vote on this item, the average rating will also be shown.
Star rating
Your vote was cast
Thank you for your feedback
Thank you for your feedback
Issue Date
2021-05-18
Metadata
Show full item recordAbstract
Sorangipyranone was isolated as a novel natural product featuring a unique 2,3-dihydro-γ-4H-pyrone scaffold from cultures of the myxobacterial strain MSr12020. We report here the full structure elucidation of sorangipyranone by spectroscopic techniques including 2D NMR and high-resolution mass spectrometry together with the analysis of the biosynthetic pathway. Determination of the absolute configuration was performed by time-dependent density functional theory-electronic circular dichroism calculations and determination of the applicability of the Snatzke's helicity rule, to correlate the high-wavelength n→π* electronic circular dichroism (ECD) transition and the absolute configuration of the 2,3-dihydro-4H-γ-pyrone, was done by the analysis of low-energy conformers and the Kohn-Sham orbitals. Sorangipyranone outlines a new class of a γ-dihydropyrone-containing natural product comprised of malonyl-CoA-derived building blocks and features a unique polyketide scaffold. In silico analysis of the genome sequence of the myxobacterial strain MSr12020 complemented with feeding experiments employing stable isotope-labeled precursors allowed the identification and annotation of a candidate biosynthetic gene cluster that encodes a modular polyketide synthase assembly line. A model for the biosynthetic pathway leading to the formation of the γ-dihydropyrone scaffold is presented in this study.Citation
Ind Microbiol Biotechnol. 2021 Jun 4;48(3-4):kuab029. doi: 10.1093/jimb/kuab029.Affiliation
HIPS, Helmholtz-Institut für Pharmazeutische Forschung Saarland, Universitätscampus E8.1 66123 Saarbrücken, Germany.Publisher
Oxford AcademicPubMed ID
34003283Type
ArticleLanguage
enEISSN
1476-5535ae974a485f413a2113503eed53cd6c53
10.1093/jimb/kuab029
Scopus Count
The following license files are associated with this item:
- Creative Commons
Related articles
- Biosynthesis and Total Synthesis of Pyrronazol B: a Secondary Metabolite from Nannocystis pusilla.
- Authors: Witte SNR, Hug JJ, Géraldy MNE, Müller R, Kalesse M
- Issue date: 2017 Nov 13
- Genome mining reveals uncommon alkylpyrones as type III PKS products from myxobacteria.
- Authors: Hug JJ, Panter F, Krug D, Müller R
- Issue date: 2019 Mar
- Myxobacterial natural product assembly lines: fascinating examples of curious biochemistry.
- Authors: Wenzel SC, Müller R
- Issue date: 2007 Dec
- Pyxipyrrolones: Structure Elucidation and Biosynthesis of Cytotoxic Myxobacterial Metabolites.
- Authors: Kjaerulff L, Raju R, Panter F, Scheid U, Garcia R, Herrmann J, Müller R
- Issue date: 2017 Aug 1
- Structure and Biosynthesis of Myxofacyclines: Unique Myxobacterial Polyketides Featuring Varing and Rare Heterocycles([]) *.
- Authors: Popoff A, Hug JJ, Walesch S, Garcia R, Keller L, Müller R
- Issue date: 2021 Dec 1