The complexation of Li+ to jasplakinolide, a marine sponge derived cyclic depsipeptide showed preferential binding to two out of four carbonyl oxygens (C-10, C-14) and the electrons of the aromatic system of the beta-tyrosine amino acid residue. This is in contrast to previous results obtained by others who proposed complexation to three out of four available carbonyl oxygens (C-1, C-10, C-14). The structure of the complex in CD3CN was determined by NOE restrained molecular dynamic calculations. Structures of the uncomplexed jasplakinolide were calculated in CDCl3 and CD3CN for comparison.
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http://dx.doi.org/10.1039/b416839a | DOI Listing |
Org Lett
January 2025
Department of Chemistry, University of Waterloo, 200 University Ave. West, Waterloo, Ontario, Canada N2L3G1.
The first total synthesis of cyclic depsipeptide antibiotic LL-A0341β (LL) is described. The configuration of the β-methyltryptophan (β-MeTrp) residue was established by preparing all four stereoisomers of Fmoc-β-MeTrp which were used for the synthesis of LL via Fmoc solid phase peptide synthesis. The most active of the four peptides was the one containing (2,3)-β-MeTrp.
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December 2024
Institute of Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing 100700, China.
Seven cyclic depsipeptides, including two new cyclic pentadepsipeptides avenamides A () and B (), were isolated from a plant-derived fungus W8 by using the bioassay-guided fractionation method. The planar structures were elucidated by using comprehensive spectroscopic analyses, including 1D and 2D NMR, as well as MS/MS spectrometry. The absolute configuration of the amino acid and hydroxy acid residues was confirmed by using the advanced Marfey's method and chiral HPLC analysis, respectively.
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November 2024
Department of Chemistry and Nanoscience, Ewha Womans University, Seoul 03760, Republic of Korea.
Three new depsipeptides, homiamides A-C (-), were isolated from a marine sediment-derived strain of sp., ROA-065. The planar structures of homiamides A-C (-) were elucidated using mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectroscopic data.
View Article and Find Full Text PDFJ Nat Prod
December 2024
Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Republic of Korea.
New lipodepsipeptides, octaminomycins C and D ( and ), were discovered in an engineered sp. strain overexpressing the LysR transcriptional regulator family. The structures of and were elucidated by comprehensive analysis of their UV, HRMS, and NMR data.
View Article and Find Full Text PDFJ Med Chem
December 2024
School of Biological Sciences, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India.
Sunshinamide, a cyclodepsipeptide, has demonstrated significant potential in inhibiting cancer cell proliferation. Our prior research established the total synthesis and anticancer properties of sunshinamide. However, a deeper understanding of the structure-activity relationship (SAR) of sunshinamide remained imperative.
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