Discovery and Total Synthesis of Doscadenamide A: A Quorum Sensing Signaling Molecule from a Marine Cyanobacterium

Xiao Liang; Susan Matthew; Qi-Yin Chen; Jason C Kwan; Valerie J Paul; Hendrik Luesch

doi:10.1021/acs.orglett.9b02525

Discovery and Total Synthesis of Doscadenamide A: A Quorum Sensing Signaling Molecule from a Marine Cyanobacterium

Org Lett. 2019 Sep 20;21(18):7274-7278. doi: 10.1021/acs.orglett.9b02525. Epub 2019 Aug 15.

Authors

Xiao Liang^{1

2}, Susan Matthew¹, Qi-Yin Chen^{1

2}, Jason C Kwan¹, Valerie J Paul³, Hendrik Luesch^{1

2}

Affiliations

¹ Department of Medicinal Chemistry , University of Florida , Gainesville , Florida 32610 , United States.
² Center for Natural Products, Drug Discovery and Development (CNPD3) , University of Florida , Gainesville , Florida 32610 , United States.
³ Smithsonian Marine Station , Fort Pierce , Florida 34949 , United States.

Abstract

Quorum sensing (QS) plays a critical role in the regulation of bacterial pathogenesis. Doscadenamide A (1a) was isolated from a marine cyanobacterium, its structure elucidated by NMR, and its activity linked to QS induction. The total synthesis of 1a was developed, and the absolute configuration confirmed through comparison of the isolated natural product with synthetic diastereomers. Our preliminary investigation indicated that 1a could activate QS signaling in a LasR-dependent manner.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Cyanobacteria / chemistry*
Drug Discovery*
Microbial Sensitivity Tests
Molecular Structure
Pseudomonas aeruginosa / drug effects*
Pyrroles / chemical synthesis
Pyrroles / chemistry
Pyrroles / pharmacology*
Quorum Sensing / drug effects
Signal Transduction / drug effects

Substances

Anti-Bacterial Agents
Pyrroles
doscadenamide A

Abstract

Publication types

MeSH terms

Substances

Grants and funding