A pair of novel lipopeptide epimers, sinulariapeptides A () and B (), and a new phthalide glycerol ether () were isolated from the marine algal-associated fungus SCSIO41401, together with three known chromanone derivates (-). The structures of the new compounds, including the absolute configurations, were determined by comprehensive spectroscopic methods, experimental and calculated electronic circular dichroism (ECD), and Mo (OAc)-induced ECD methods. The new compounds - showed moderate inhibitory activity against acetylcholinesterase (AChE), with IC values of 1.3-2.5 μM, and an in silico molecular docking study was also performed.
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http://dx.doi.org/10.3390/md18110547 | DOI Listing |
J Am Chem Soc
July 2021
Laboratorium für Organische Chemie, ETH Zürich, D-CHAB, Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
Mutanobactin D is a non-ribosomal, cyclic peptide isolated from and shows activity reducing yeast-to-hyphae transition as well as biofilm formation of the pathogenic yeast . We report the first total synthesis of this natural product, which relies on enantioselective, zinc-mediated 1,3-dipolar cycloaddition and a sequence of cascading reactions, providing the key lipidated γ-amino acid found in mutanobactin D. The synthesis enables configurational assignment, determination of the dominant solution-state structure, and studies to assess the stability of the lipopeptide substructure found in the natural product.
View Article and Find Full Text PDFMar Drugs
October 2020
CAS Key Laboratory of Tropical Marine Bio-resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China.
A pair of novel lipopeptide epimers, sinulariapeptides A () and B (), and a new phthalide glycerol ether () were isolated from the marine algal-associated fungus SCSIO41401, together with three known chromanone derivates (-). The structures of the new compounds, including the absolute configurations, were determined by comprehensive spectroscopic methods, experimental and calculated electronic circular dichroism (ECD), and Mo (OAc)-induced ECD methods. The new compounds - showed moderate inhibitory activity against acetylcholinesterase (AChE), with IC values of 1.
View Article and Find Full Text PDFBioorg Med Chem
January 2019
Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, Ontario N2L 3G1, Canada. Electronic address:
Daptomycin, a cyclic lipodepsipeptide antibiotic, has been used clinically since 2003 to treat serious infections caused by Gram-positive bacteria. Although 37 years have passed since daptomycin's discovery, its mechanism of action is still debated. In this report, the effect of replacing the ester bond with an amide bond, and overall stereochemistry, on daptomycin's biological activity was examined.
View Article and Find Full Text PDFBioorg Med Chem Lett
August 2016
Bio-organic Synthesis, Leiden Institute of Chemistry, Leiden University, The Netherlands.
Chirally pure R- and S-epimers of TLR2 ligand Pam3CysSK4 were prepared and separately conjugated to an OVA model epitope, in which lysine was replaced by azidonorleucine. The azide function in the conjugate permitted labelling with different fluorophores by use of strain-promoted 3+2 cycloaddition. The R-epimer of the labelled conjugates induced TLR2-dependent DC maturation, while S-epimer proved to be inactive.
View Article and Find Full Text PDFChembiochem
December 2014
NMR and Structure Analysis Unit, Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000 Ghent (Belgium).
The viscosin group covers a series of cyclic lipodepsipeptides (CLPs) produced by Pseudomonas bacteria, with a range of biological functions and antimicrobial activities. Their oligopeptide moieties are composed of both L- and D-amino acids. Remarkably, the Leu5 amino acid-centrally located in the nonapeptide sequence-is the sole residue found to possess either an L or D configuration, depending on the producing strain.
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