2-Hydroxysorangiadenosine: Structure and Biosynthesis of a Myxobacterial Sesquiterpene-Nucleoside.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Dorothy A OkothRolf Müller

Abstract

Myxobacteria represent an under-investigated source for biologically active natural products featuring intriguing structural moieties with potential applications, e.g., in the pharmaceutical industry. Sorangiadenosine and the here-discovered 2-hydroxysorangiadenosine are myxobacterial sesquiterpene-nucleosides with an unusual structural moiety, a bicyclic eudesmane-type sesquiterpene. As the biosynthesis of these rare terpene-nucleoside hybrid natural products remains elusive, we investigated secondary metabolomes and genomes of several 2-hydroxysorangiadenosine-producing myxobacteria. We report the isolation and full structure elucidation of 2-hydroxysorangiadenosine and its cytotoxic and antibiotic activities and propose a biosynthetic pathway in the myxobacterium Vitiosangium cumulatum MCy10943T.

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Citations

Nov 11, 2020·Natural Product Reports·Jeffrey D RudolfZining Li
May 19, 2021·Journal of Industrial Microbiology & Biotechnology·Dorothy A OkothRolf Müller
Nov 11, 2020·Analytical Chemistry·Chantal D BaderRolf Müller
Aug 29, 2021·Pharmaceutics·Mudasir Ahmad BhatArif Tasleem Jan
Nov 20, 2021·ACS Catalysis·Baofu XuJeffrey D Rudolf

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Datasets Mentioned

BETA
MT520811

Methods Mentioned

BETA
nuclear magnetic resonance
NMR
circular dichroism
metabolomic profiling

Software Mentioned

HyStar
antiSMASH )
BLAST
ChemSpider
blastx
ChEMBL
Pfam
DataAnalysis
antiSMASH
RS Remote

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