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Published on: February 25, 2021
Total structure determination of grassypeptolide, a new marine cyanobacterial cytotoxin
Jason C Kwan1, James R Rocca, Khalil A Abboud
1Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610, USA.
Abstract:
A collection of the cyanobacterium Lyngbya confervoides off Grassy Key in Florida yielded grassypeptolide (1), a 31-membered macrocyclic depsipeptide with unusually high D-amino acid content, two thiazolines, and one beta-amino acid. We report the rigorous 3D structure determination and conformational analysis in solution and solid state by NMR, MS, X-ray crystallography, chemical degradation, and molecular modeling involving distance geometry and restrained molecular dynamics. Grassypeptolide (1) inhibited cancer cell growth with IC50 values from 1.0 to 4.2 microM.
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