Pseudouridimycin TFA | CAS#2760807-99-4 | antibiotic

MedKoo Cat#: 585038 | Name: Pseudouridimycin TFA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pseudouridimycin (PUM) is an antibiotic that inhibits bacterial RNA polymerase (RNAP). It is a nucleoside analog that is effective against both Gram-positive and Gram-negative bacteria. PUM has a low rate of resistance acquisition and a wide range of antibacterial activity. It is shown that PUM particularly inhibits bRNAP in vitro, with an IC50 of ∼0.1 μM and also with a minimum inhibitory concentration (MIC) of 4 to 6 μg/mL. In vitro bactericidal activity is reported for PUM against drug-sensitive, drug-resistant, and multidrug-resistant Streptococcus species.

Chemical Structure

Pseudouridimycin TFA

CAS#2760807-99-4 (TFA)

Theoretical Analysis

MedKoo Cat#: 585038

Name: Pseudouridimycin TFA

CAS#: 2760807-99-4 (TFA)

Chemical Formula: C19H27F3N8O11

Exact Mass: 0.0000

Molecular Weight: 600.47

Elemental Analysis: C, 38.01; H, 4.53; F, 9.49; N, 18.66; O, 29.31

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

2760807-99-4 (TFA) 1566586-52-4 (free base)

Synonym

Pseudouridimycin; PUM

IUPAC/Chemical Name

(S)-N1-(((2R,3S,4R,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-2-(2-guanidino-N-hydroxyacetamido)pentanediamide 2,2,2-trifluoroacetate

InChi Key

QVDKLWNBWGUBHE-XFMFGANJSA-N

InChi Code

InChI=1S/C17H26N8O9.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t7-,8+,11+,12+,13-;/m0./s1

SMILES Code

C(C(O)=O)(F)(F)F.O[C@H]1[C@@H](O[C@H](CNC([C@@H](N(C(CNC(=N)N)=O)O)CCC(N)=O)=O)[C@H]1O)C=2C(=O)NC(=O)NC2

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 600.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: 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. 2024 Jan 2;19(1):e202300474. doi: 10.1002/cmdc.202300474. Epub 2023 Oct 6. PMID: 37751316; PMCID: PMC10843019. 2: Artukka E, Schnell R, Palmu K, Rosenqvist P, Szodorai E, Niemi J, Virta P, Schneider G, Metsä-Ketelä M. Pseudouridine-Modifying Enzymes SapB and SapH Control Entry into the Pseudouridimycin Biosynthetic Pathway. ACS Chem Biol. 2023 Apr 21;18(4):794-802. doi: 10.1021/acschembio.2c00826. Epub 2023 Apr 2. PMID: 37005433; PMCID: PMC10127198. 3: Pavundurai Chandra K, Perumal D, Ragunathan P. Pseudouridimycin-A Potent Nucleoside Inhibitor of the RNA Polymerase Beta Prime Subunit of Streptococcus pyogenes. ACS Omega. 2023 Feb 13;8(8):7989-8000. doi: 10.1021/acsomega.2c07805. PMID: 36873015; PMCID: PMC9979225. 4: Okawa R, Aldrich CC, Ichikawa S. Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction. Chem Commun (Camb). 2022 Jul 14;58(57):7956-7959. doi: 10.1039/d2cc02442j. PMID: 35757838. 5: H Rabbad A, Agoni C, E Soliman M. Structural Insights into the Role of Pseudouridimycin Binding in Disruption of Bacterial RNA Polymerase Bridge Helix Conformational Arrangement. Curr Pharm Biotechnol. 2023;24(4):562-569. doi: 10.2174/1389201023666220511211433. PMID: 35546759. 6: Cain CF, Scott AM, Sarnowski MP, Del Valle JR. Correction: Total synthesis and chemical stability of pseudouridimycin. Chem Commun (Camb). 2022 Feb 22;58(16):2762. doi: 10.1039/d2cc90056d. Erratum for: Chem Commun (Camb). 2022 Feb 15;58(14):2351-2354. doi: 10.1039/d1cc07059b. PMID: 35141739. 7: Cain CF, Scott AM, Sarnowski MP, Del Valle JR. Total synthesis and chemical stability of pseudouridimycin. Chem Commun (Camb). 2022 Feb 15;58(14):2351-2354. doi: 10.1039/d1cc07059b. Erratum in: Chem Commun (Camb). 2022 Feb 22;58(16):2762. doi: 10.1039/d2cc90056d. PMID: 35080211. 8: Wang XK, Jia YM, Li YX, Yu CY. Total Synthesis of Pseudouridimycin. Org Lett. 2022 Jan 21;24(2):511-515. doi: 10.1021/acs.orglett.1c03914. Epub 2022 Jan 10. PMID: 35005956. 9: Vela Gurovic MS, Díaz ML, Gallo CA, Dietrich J. Phylogenomics, CAZyome and core secondary metabolome of Streptomyces albus species. Mol Genet Genomics. 2021 Nov;296(6):1299-1311. doi: 10.1007/s00438-021-01823-9. Epub 2021 Sep 26. PMID: 34564766. 10: Iorio M, Davatgarbenam S, Serina S, Criscenzo P, Zdouc MM, Simone M, Maffioli SI, Ebright RH, Donadio S, Sosio M. Blocks in the pseudouridimycin pathway unlock hidden metabolites in the Streptomyces producer strain. Sci Rep. 2021 Mar 12;11(1):5827. doi: 10.1038/s41598-021-84833-2. PMID: 33712632; PMCID: PMC7955054. 11: Zdouc MM, Iorio M, Vind K, Simone M, Serina S, Brunati C, Monciardini P, Tocchetti A, Zarazúa GS, Crüsemann M, Maffioli SI, Sosio M, Donadio S. Effective approaches to discover new microbial metabolites in a large strain library. J Ind Microbiol Biotechnol. 2021 Jun 4;48(3-4):kuab017. doi: 10.1093/jimb/kuab017. PMID: 33599744; PMCID: PMC9113118. 12: Böhringer N, Patras MA, Schäberle TF. Heterologous Expression of Pseudouridimycin and Description of the Corresponding Minimal Biosynthetic Gene Cluster. Molecules. 2021 Jan 19;26(2):510. doi: 10.3390/molecules26020510. PMID: 33478059; PMCID: PMC7835738. 13: Shiraishi T, Kuzuyama T. Recent advances in the biosynthesis of nucleoside antibiotics. J Antibiot (Tokyo). 2019 Dec;72(12):913-923. doi: 10.1038/s41429-019-0236-2. Epub 2019 Sep 25. PMID: 31554958. 14: Rosenqvist P, Palmu K, Prajapati RK, Yamada K, Niemi J, Belogurov GA, Metsä- Ketelä M, Virta P. Characterization of C-nucleoside Antimicrobials from Streptomyces albus DSM 40763: Strepturidin is Pseudouridimycin. Sci Rep. 2019 Jun 20;9(1):8935. doi: 10.1038/s41598-019-45375-w. PMID: 31222036; PMCID: PMC6586884. 15: Maffioli SI, Sosio M, Ebright RH, Donadio S. Discovery, properties, and biosynthesis of pseudouridimycin, an antibacterial nucleoside-analog inhibitor of bacterial RNA polymerase. J Ind Microbiol Biotechnol. 2019 Mar;46(3-4):335-343. doi: 10.1007/s10295-018-2109-2. Epub 2018 Nov 21. PMID: 30465105; PMCID: PMC6405294. 16: Rabbad AH, Agoni C, Olotu FA, Soliman ME. Microbes, not humans: exploring the molecular basis of Pseudouridimycin selectivity towards bacterial and not human RNA polymerase. Biotechnol Lett. 2019 Jan;41(1):115-128. doi: 10.1007/s10529-018-2617-1. Epub 2018 Oct 30. PMID: 30377869. 17: O'Malley PA. Pseudouridimycin: Light in the Darkness of Antimicrobial Resistance. Clin Nurse Spec. 2018 May/Jun;32(3):114-115. doi: 10.1097/NUR.0000000000000367. PMID: 29621104. 18: Sosio M, Gaspari E, Iorio M, Pessina S, Medema MH, Bernasconi A, Simone M, Maffioli SI, Ebright RH, Donadio S. Analysis of the Pseudouridimycin Biosynthetic Pathway Provides Insights into the Formation of C-nucleoside Antibiotics. Cell Chem Biol. 2018 May 17;25(5):540-549.e4. doi: 10.1016/j.chembiol.2018.02.008. Epub 2018 Mar 15. PMID: 29551347; PMCID: PMC5959762. 19: Ebright RH. Novel RNA polymerase inhibitor found in soil extracts provides hope for future antibacterial drugs. Future Med Chem. 2017 Oct;9(16):1857-1861. doi: 10.4155/fmc-2017-0188. Epub 2017 Oct 27. PMID: 29076390. 20: Chellat MF, Riedl R. Pseudouridimycin: The First Nucleoside Analogue That Selectively Inhibits Bacterial RNA Polymerase. Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13184-13186. doi: 10.1002/anie.201708133. Epub 2017 Sep 12. PMID: 28895263.