Solution-phase syntheses of three bioactive natural products of mixed polypeptide-polyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5303010PMC
http://dx.doi.org/10.1039/c6ob01233gDOI Listing

Publication Analysis

Top Keywords

synthesis fellutamides
8
total synthesis
4
fellutamides lipopeptide
4
lipopeptide proteasome
4
proteasome inhibitors
4
inhibitors sustainable
4
sustainable peptide
4
peptide bond
4
bond formation
4
formation solution-phase
4

Similar Publications

Unlabelled: Secondary metabolites (SMs) are biologically active small molecules, many of which are medically valuable. Fungal genomes contain vast numbers of SM biosynthetic gene clusters (BGCs) with unknown products, suggesting that huge numbers of valuable SMs remain to be discovered. It is challenging, however, to identify SM BGCs, among the millions present in fungi, that produce useful compounds.

View Article and Find Full Text PDF

The antifungal echinocandin lipopeptide, acrophiarin, was circumscribed in a patent in 1979. We confirmed that the producing strain NRRL 8095 is Penicillium arenicola and other strains of P. arenicola produced acrophiarin and acrophiarin analogues.

View Article and Find Full Text PDF

Identification of Secondary Metabolites from by Untargeted UPLC-ESI-HRMS/MS and Genome Mining.

Molecules

February 2020

Texas Therapeutic Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, Houston, TX 77054, USA.

is an industrially important fungus for the production of the antifungal echinocandin B and is closely related to model organism . Its secondary metabolism is largely unknown except for the production of echinocandin B and sterigmatocystin. We constructed mutants for three genes that regulate secondary metabolism in NRRL 11440, and evaluated the secondary metabolites produced by wild type and mutants strains.

View Article and Find Full Text PDF

Resistance Gene-Directed Genome Mining of 50 Species.

mSystems

May 2019

Department of Biotechnology and Biomedicine, Technical University of Denmark, Kongens Lyngby, Denmark.

Fungal secondary metabolites are a rich source of valuable natural products, and genome sequencing has revealed a proliferation of predicted biosynthetic gene clusters in the genomes. However, it is currently an unfeasible task to characterize all biosynthetic gene clusters and to identify possible uses of the compounds. Therefore, a rational approach is needed to identify a short list of gene clusters responsible for producing valuable compounds.

View Article and Find Full Text PDF

Fellutamide B is reported to have cytotoxic and proteasome inhibitory activity. Interestingly, fellutamide B and its simplified analogues have also been observed for the neurotrophic activity by stimulating the synthesis and secretion of neurotrophins. Owing to the interesting structural and potent neurotrophic role of fellutamide B (a lipopeptide aldehyde), we have assessed the synthetic path intermediates (compounds A-D) of fellutamide B for their neuroactive potential (in vitro and in vivo).

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!