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Chemical Modification of Pactamycin Leads to New Compounds with Retained Antimicrobial Activity and Reduced Toxicity.
Molecules
September 2024
Synthetic Organic Chemistry Laboratory, Department of Chemistry, University of Patras, 26504 Patras, Greece.
Pactamycin (PCT), an antibiotic produced by , is a five-membered ring aminocyclitol that is active against a variety of Gram-positive and Gram-negative microorganisms, as well as several animal tumor lines in culture and in vivo. Pactamycin targets the small ribosomal subunit and inhibits protein synthesis in bacteria, archaea, and eukaryotes, but due to its toxicity is used only as a tool for biochemical research. Prompted by the successful and well-established procedure for the derivatization of antibiotics, we modified pactamycin by tethering basic amino acids to the free primary amino group of the aminocyclitol ring.
View Article and Find Full Text PDFProgress toward the Total Synthesis of Jogyamycin Using a Tandem Ichikawa/Winstein Rearrangement.
Org Lett
November 2023
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Jogyamycin is a densely functionalized aminocyclopentitol that displays potent antiprotozoal activity. Herein, we report a route toward this natural product that utilizes an unprecedented transformation involving a tandem Ichikawa-Winstein rearrangement to install the C-1/C-2 diamine core. Attempts to further functionalize the C-3/C-4 alkene en route to jogyamycin are also discussed.
View Article and Find Full Text PDFStereo-Controlled Synthesis of Vicinal Tertiary Carbinols: Application in the Synthesis of a Diol Substructure of Zaragozic Acid, Pactamycin and Ryanodol.
Chemistry
September 2023
Department of Chemistry, Seoul National University, Gwanak-1 Gwanak-ro, Gwanak-gu, Seoul, 08826, South Korea.
A novel and flexible approach for the stereo-controlled synthesis of vicinal tertiary carbinols is reported. The developed strategy featured a highly diastereoselective singlet-oxygen (O ) [4+2] cycloaddition of rationally designed cyclohexadienones (derived from oxidative dearomatization of the corresponding carboxylic-acid appended phenol precursors), followed by programmed "O-O" and "C-C" bond cleavage. In doing so, a highly functionalized and versatile intermediate was identified and prepared in synthetically useful quantity as a plausible precursor to access a variety of designed and naturally occurring vicinal tertiary carbinol containing compounds.
View Article and Find Full Text PDFModifications of Acyl Carrier Protein-Bound Glycosylated Polyketides in Pactamycin Biosynthesis.
Chemistry
June 2023
Department of Pharmaceutical Sciences, Oregon State University, 203 Pharmacy Building, Corvallis, Oregon, 97331-3507, USA.
The potent antitumor antibiotic pactamycin is an aminocyclopentitol-containing natural product produced by the soil bacterium Streptomyces pactum. Recent studies showed that the aminocyclopentitol unit is derived from N-acetyl-D-glucosamine, which is attached to an acyl carrier protein (ACP)-bound polyketide by a glycosyltransferase enzyme, PtmJ. Here, we report a series of post-glycosylation modifications of the sugar moiety of the glycosylated polyketide while it is still attached to the carrier protein.
View Article and Find Full Text PDFModulation of Specialized Metabolite Production in Genetically Engineered .
ACS Chem Biol
November 2021
Department of Pharmaceutical Sciences, Oregon State University, Corvallis, Oregon 97331-3507 United States.
Filamentous soil bacteria are known to produce diverse specialized metabolites. Despite having enormous potential as a source of pharmaceuticals, they often produce bioactive metabolites at low titers. Here, we show that inactivation of the pactamycin, NFAT-133, and conglobatin biosynthetic pathways in ATCC 27456 significantly increases the production of the mitochondrial electron transport inhibitors piericidins.
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