Reconsidering the Structure of Serlyticin-A

Ka Yi Tsui, Robert J. Tombari, David E. Olson, Dean J. Tantillo

Research output: Contribution to journalArticle

Abstract

Serlyticin-A is a secondary metabolite first isolated from a culture of Serratia ureilytica grown using squid pen as the sole carbon/nitrogen source. A previous study by Kuo et al. demonstrated that it has antioxidative and antiproliferative properties. However, the proposed chemical structure of serlyticin-A is likely incorrect based on the thermodynamic instability of its three contiguous heteroatom-heteroatom bonds. Here, we use quantum chemical calculations to predict 1H and 13C chemical shifts for serlyticin-A and demonstrate a discrepancy between the calculated and experimental chemical shifts. We then propose several reasonable alternative structures for serlyticin-A. Considering the known antioxidant and antiproliferative activity of hydroxamic acids as well as their stability and prevalence in natural products of bacterial origin, we believe that serlyticin-A is most likely 3-indolylacetohydroxamic acid (4). We provide our rationale for this assignment as well as experimental data for pure 3-indolylacetohydroxamic acid obtained via de novo synthesis. This study highlights the power of computational NMR shift prediction to revise chemical structures for natural products like serlyticin-A.

Original languageEnglish (US)
Pages (from-to)3464-3468
Number of pages5
JournalJournal of Natural Products
Volume82
Issue number12
DOIs
StatePublished - Dec 27 2019

Fingerprint

Chemical shift
Biological Products
Hydroxamic Acids
Serratia
Decapodiformes
Acids
Metabolites
Thermodynamics
Nitrogen
Carbon
Antioxidants
Nuclear magnetic resonance

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

Cite this

Reconsidering the Structure of Serlyticin-A. / Tsui, Ka Yi; Tombari, Robert J.; Olson, David E.; Tantillo, Dean J.

In: Journal of Natural Products, Vol. 82, No. 12, 27.12.2019, p. 3464-3468.

Research output: Contribution to journalArticle

Tsui, Ka Yi ; Tombari, Robert J. ; Olson, David E. ; Tantillo, Dean J. / Reconsidering the Structure of Serlyticin-A. In: Journal of Natural Products. 2019 ; Vol. 82, No. 12. pp. 3464-3468.
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