Pseudouridimycin Explained

Drug Name:Pseudouridimycin
Legal Status:Investigational
C:17
H:26
N:8
O:9
Iupac Name:(2S)-2-2-(diaminomethylideneamino)acetyl-hydroxyamino]-N-(2R,3S,4R,5S)-5-(2,4-dioxo-1H-pyrimidin-5-yl)-3,4-dihydroxyoxolan-2-ylmethyl]pentanediamide
Cas Number:1566586-52-4
Chemspiderid:59651398
Pubchem:72792467
Chebi:199549
Pdb Ligand:PUM
Smiles:C1=C(C(=O)NC(=O)N1)[C@H]2[C@@H]([C@@H]([C@H](O2)CNC(=O)[C@H](CCC(=O)N)N(C(=O)CN=C(N)N)O)O)O
Stdinchi:1S/C17H26N8O9/c18-9(26)2-1-7(25(33)10(27)5-22-16(19)20)15(31)21-4-8-11(28)12(29)13(34-8)6-3-23-17(32)24-14(6)30/h3,7-8,11-13,28-29,33H,1-2,4-5H2,(H2,18,26)(H,21,31)(H4,19,20,22)(H2,23,24,30,32)/t7-,8+,11+,12+,13-/m0/s1
Stdinchikey:XDEYHXABZOKKDZ-YFKLLHAASA-N

Pseudouridimycin (PUM) is an experimental antibiotic isolated from the soil bacteria Streptomyces albus. It inhibits bacterial RNA polymerase through a different mechanism from previously discovered drugs. Pseudouridimycin shows useful activity against pathogens such as multidrug-resistant Streptococcus pyogenes, and while it is unclear whether it will be suitable for development for medical use in its own right, modified derivatives have been produced with improved stability and similar antibiotic properties.[1] [2] [3] [4] [5]

See also

Notes and References

  1. Chellat MF, Riedl R . Pseudouridimycin: The First Nucleoside Analogue That Selectively Inhibits Bacterial RNA Polymerase . Angewandte Chemie . 56 . 43 . 13184–13186 . October 2017 . 10.1002/anie.201708133 . 28895263 .
  2. Maffioli SI, Sosio M, Ebright RH, Donadio S . Discovery, properties, and biosynthesis of pseudouridimycin, an antibacterial nucleoside-analog inhibitor of bacterial RNA polymerase . Journal of Industrial Microbiology & Biotechnology . 46 . 3–4 . 335–343 . March 2019 . 10.1007/s10295-018-2109-2 . 30465105 . 6405294 .
  3. Wang XK, Jia YM, Li YX, Yu CY . Total Synthesis of Pseudouridimycin . Organic Letters . 24 . 2 . 511–515 . January 2022 . 10.1021/acs.orglett.1c03914 . 35005956 .
  4. Pavundurai Chandra K, Perumal D, Ragunathan P . Pseudouridimycin-A Potent Nucleoside Inhibitor of the RNA Polymerase Beta Prime Subunit of Streptococcus pyogenes . ACS Omega . 8 . 8 . 7989–8000 . February 2023 . 10.1021/acsomega.2c07805 . 36873015 . 9979225 .
  5. Anwar AF, Cain CF, Garza MJ, Degen D, Ebright RH, Del Valle JR . Stabilizing Pseudouridimycin: Synthesis, RNA Polymerase Inhibitory Activity, and Antibacterial Activity of Dipeptide-Modified Analogues . ChemMedChem . 19 . 1 . e202300474 . January 2024 . 10.1002/cmdc.202300474 . 37751316 . 10843019 . January 2, 2025 .

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