2-Thiouridine | CAS# 20235-78-3 | Nucleosides

MedKoo Cat#: 122474 | Name: 2-Thiouridine

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Description:

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

2-Thiouridine is a thiouridine and a nucleoside analogue.

Chemical Structure

2-Thiouridine

CAS#20235-78-3

Theoretical Analysis

MedKoo Cat#: 122474

Name: 2-Thiouridine

CAS#: 20235-78-3

Chemical Formula: C9H12N2O5S

Exact Mass: 260.0467

Molecular Weight: 260.26

Elemental Analysis: C, 41.53; H, 4.65; N, 10.76; O, 30.74; S, 12.32

Price and Availability

Size	Price	Availability
100mg	USD 250.00	2 Weeks
250mg	USD 550.00	2 Weeks
500mg	USD 750.00	2 Weeks
1g	USD 1,150.00	2 Weeks

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Related CAS #

No Data

Synonym

2-thiouridine; Uridine, 2-thio-; 1-beta-D-ribofuranosyl-2-thiouracil

IUPAC/Chemical Name

1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

InChi Key

GJTBSTBJLVYKAU-XVFCMESISA-N

InChi Code

InChI=1S/C9H12N2O5S/c12-3-4-6(14)7(15)8(16-4)11-2-1-5(13)10-9(11)17/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,17)/t4-,6-,7-,8-/m1/s1

SMILES Code

OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N(C(N2)=S)C=CC2=O)O1

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 260.26 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: Edwards AM, Black KA, Dos Santos PC. Sulfur Availability Impacts Accumulation of the 2-Thiouridine tRNA Modification in Bacillus subtilis. J Bacteriol. 2022 May 17;204(5):e0000922. doi: 10.1128/jb.00009-22. Epub 2022 Apr 25. PMID: 35467390; PMCID: PMC9112905. 2: Masaki Y, Yamamoto K, Inde T, Yoshida K, Maruyama A, Nagata T, Tanihata J, Takeda S, Sekine M, Seio K. Synthesis of 2'-O-(N-methylcarbamoylethyl) 5-methyl-2-thiouridine and its application to splice-switching oligonucleotides. Bioorg Med Chem Lett. 2019 Jan 15;29(2):160-163. doi: 10.1016/j.bmcl.2018.12.005. Epub 2018 Dec 4. PMID: 30551900. 3: Lentini JM, Fu D. Monitoring the 5-Methoxycarbonylmethyl-2-Thiouridine (mcm5s2U) Modification Utilizing the Gamma-Toxin Endonuclease. Methods Mol Biol. 2021;2298:197-216. doi: 10.1007/978-1-0716-1374-0_13. PMID: 34085247. 4: Wang R, Haruehanroengra P, Sheng J. Synthesis of Geranyl-2-Thiouridine- Modified RNA. Curr Protoc Nucleic Acid Chem. 2017 Mar 2;68:4.72.1-4.72.13. doi: 10.1002/cpnc.22. PMID: 28252182. 5: Xu J, Green NJ, Gibard C, Krishnamurthy R, Sutherland JD. Prebiotic phosphorylation of 2-thiouridine provides either nucleotides or DNA building blocks via photoreduction. Nat Chem. 2019 May;11(5):457-462. doi: 10.1038/s41557-019-0225-x. Epub 2019 Apr 1. PMID: 30936523; PMCID: PMC6597365. 6: Rogers KC, Crescenzo AT, Söll D. Aminoacylation of transfer RNAs with 2-thiouridine derivatives in the wobble position of the anticodon. Biochimie. 1995;77(1-2):66-74. doi: 10.1016/0300-9084(96)88106-5. PMID: 7541255. 7: Larsen AT, Fahrenbach AC, Sheng J, Pian J, Szostak JW. Thermodynamic insights into 2-thiouridine-enhanced RNA hybridization. Nucleic Acids Res. 2015 Sep 18;43(16):7675-87. doi: 10.1093/nar/gkv761. Epub 2015 Aug 3. PMID: 26240387; PMCID: PMC4652770. 8: Abou-Elkhair RAI, Du J, Wasfy AA, Khaill NA, Maaroof HM, Hassan MH, Ahmed AS, Hassan AEA, Sheng J. Synthesis of 6-Aza-2-Hydroxyimino-5-Methylpyrimidine Nucleosides for Antiviral Evaluation. Curr Protoc. 2021 Dec;1(12):e329. doi: 10.1002/cpz1.329. PMID: 34878712. 9: Bartos P, Maciaszek A, Rosinska A, Sochacka E, Nawrot B. Transformation of a wobble 2-thiouridine to 2-selenouridine via S-geranyl-2-thiouridine as a possible cellular pathway. Bioorg Chem. 2014 Oct;56:49-53. doi: 10.1016/j.bioorg.2014.05.012. Epub 2014 Jun 6. PMID: 24971911. 10: Black KA, Dos Santos PC. Abbreviated Pathway for Biosynthesis of 2-Thiouridine in Bacillus subtilis. J Bacteriol. 2015 Jun;197(11):1952-62. doi: 10.1128/JB.02625-14. Epub 2015 Mar 30. PMID: 25825430; PMCID: PMC4420905. 11: Carlucci M, Kierzek E, Olejnik A, Turner DH, Kierzek R. Chemical synthesis of LNA-2-thiouridine and its influence on stability and selectivity of oligonucleotide binding to RNA. Biochemistry. 2009 Nov 24;48(46):10882-93. doi: 10.1021/bi901506f. PMID: 19835380; PMCID: PMC2839159. 12: Rayala R, Giuglio-Tonolo A, Broggi J, Terme T, Vanelle P, Theard P, Médebielle M, Wnuk SF. Studies toward the oxidative and reductive activation of C-S bonds in 2'-S-aryl-2'-thiouridine derivatives. Tetrahedron. 2016 Apr 21;72(16):1969-1977. doi: 10.1016/j.tet.2016.02.063. PMID: 27019535; PMCID: PMC4806340. 13: Kulik K, Sadowska K, Wielgus E, Pacholczyk-Sienicka B, Sochacka E, Nawrot B. 2-Selenouridine, a Modified Nucleoside of Bacterial tRNAs, Its Reactivity in the Presence of Oxidizing and Reducing Reagents. Int J Mol Sci. 2022 Jul 19;23(14):7973. doi: 10.3390/ijms23147973. PMID: 35887319; PMCID: PMC9325004. 14: Lentini JM, Ramos J, Fu D. Monitoring the 5-methoxycarbonylmethyl-2-thiouridine (mcm5s2U) modification in eukaryotic tRNAs via the γ-toxin endonuclease. RNA. 2018 May;24(5):749-758. doi: 10.1261/rna.065581.118. Epub 2018 Feb 13. PMID: 29440318; PMCID: PMC5900570. 15: Sierant M, Leszczynska G, Sadowska K, Dziergowska A, Rozanski M, Sochacka E, Nawrot B. S-Geranyl-2-thiouridine wobble nucleosides of bacterial tRNAs; chemical and enzymatic synthesis of S-geranylated-RNAs and their physicochemical characterization. Nucleic Acids Res. 2016 Dec 15;44(22):10986-10998. doi: 10.1093/nar/gkw727. Epub 2016 Aug 26. PMID: 27566149; PMCID: PMC5159532. 16: Termathe M, Leidel SA. Urm1: A Non-Canonical UBL. Biomolecules. 2021 Jan 22;11(2):139. doi: 10.3390/biom11020139. PMID: 33499055; PMCID: PMC7911844. 17: Masaki Y, Miyasaka R, Hirai K, Kanamori T, Tsunoda H, Ohkubo A, Seio K, Sekine M. Properties of 5- and/or 2-modified 2'-O-cyanoethyl uridine residue: 2'-O-cyanoethyl-5-propynyl-2-thiouridine as an efficient duplex stabilizing component. Org Biomol Chem. 2014 Feb 21;12(7):1157-62. doi: 10.1039/c3ob41983e. PMID: 24407113. 18: Sochacka E, Kraszewska K, Sochacki M, Sobczak M, Janicka M, Nawrot B. The 2-thiouridine unit in the RNA strand is desulfured predominantly to 4-pyrimidinone nucleoside under in vitro oxidative stress conditions. Chem Commun (Camb). 2011 May 7;47(17):4914-6. doi: 10.1039/c1cc10973a. Epub 2011 Mar 24. PMID: 21431224. 19: Okamoto I, Seio K, Sekine M. Triplex forming ability of oligonucleotides containing 2'-O-methyl-2-thiouridine or 2-thiothymidine. Bioorg Med Chem Lett. 2006 Jun 15;16(12):3334-6. doi: 10.1016/j.bmcl.2006.02.019. Epub 2006 May 2. PMID: 16631365. 20: Shohda K, Okamoto I, Wada T, Seio K, Sekine M. Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2-thiouridine. Bioorg Med Chem Lett. 2000 Aug 21;10(16):1795-8. doi: 10.1016/s0960-894x(00)00342-5. PMID: 10969970.