Pseudouridimycin

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

MedKoo CAT#: 585038

CAS#: 1566586-52-4

Description: Pseudouridimycin is a nucleoside analogue that selectively inhibits bacterial RNA polymerase.

Chemical Structure

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Pseudouridimycin
CAS# 1566586-52-4
Instruction

Theoretical Analysis

MedKoo Cat#: 585038
Name: Pseudouridimycin
CAS#: 1566586-52-4
Chemical Formula: C17H26N8O9
Exact Mass: 486.18
Molecular Weight: 486.442
Elemental Analysis: C, 41.98; H, 5.39; N, 23.04; O, 29.60

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Pseudouridimycin; PUM

IUPAC/Chemical Name: 2,4(1H,3H)-Pyrimidinedione, 5-(5-((N-(aminoiminomethyl)glycyl-N2-hydroxy-L-glutaminyl)amino)-5-deoxy-beta-D-ribofuranosyl)-

InChi Key: XDEYHXABZOKKDZ-YFKLLHAASA-N

InChi Code: InChI=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

SMILES Code: O=C1NC(C([C@H]2[C@@H]([C@@H]([C@@H](CNC([C@H](CCC(N)=O)N(C(CNC(N)=N)=O)O)=O)O2)O)O)=CN1)=O

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 486.44 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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. PubMed PMID: 28895263.

2: Maffioli SI, Zhang Y, Degen D, Carzaniga T, Del Gatto G, Serina S, Monciardini P, Mazzetti C, Guglierame P, Candiani G, Chiriac AI, Facchetti G, Kaltofen P, Sahl HG, Dehò G, Donadio S, Ebright RH. Antibacterial Nucleoside-Analog Inhibitor of Bacterial RNA Polymerase. Cell. 2017 Jun 15;169(7):1240-1248.e23. doi: 10.1016/j.cell.2017.05.042. PubMed PMID: 28622509; PubMed Central PMCID: PMC5542026.

3: 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. PubMed PMID: 29621104.

4: 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. PubMed PMID: 29551347; PubMed Central PMCID: PMC5959762.

5: 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. Review. PubMed PMID: 30465105; PubMed Central PMCID: PMC6405294.

6: 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. PubMed PMID: 31222036; PubMed Central PMCID: PMC6586884.

7: 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. PubMed PMID: 30377869.

8: 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. PubMed PMID: 29076390.