20235-78-3

Basic information

• Product Name: 2-THIOURIDINE
• Synonyms: 2-THIOURIDINE;2-Thio-D-uridine;2-Thioxo-2-deoxouridine;1-β-D-Ribofuranosyl-2-thiouracil;1-beta-D-Ribofuranosyl-2-thiouracil;Uridine, 2-thio-
• CAS NO: 20235-78-3
• Molecular Formula: C₉H₁₂N₂O₅S
• Molecular Weight: 260.27
• Product Categories: Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Sulfur & Selenium Compounds
• Mol File: 20235-78-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 216-218°C
• Appearance: white solid
• Density: 1.72±0.1 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.732
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly, Heated), Water (Slightly, Heated)
• PKA: 6.98±0.20(Predicted)
• CAS DataBase Reference: 2-THIOURIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-THIOURIDINE(20235-78-3)
• EPA Substance Registry System: 2-THIOURIDINE(20235-78-3)

Safety Data

• Hazardous Substances Data: 20235-78-3(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Modified nucleotide, essential for normal cell growth in some bacterial species. This compound is also able to chelate several metal ions.

InChI:InChI=1/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

Upstream product

• 59495-20-4 4-ethoxy-1-(β-D-ribofuranosyl)-2(1H)-pyrimidinone 
• 13233-20-0 2-thiocytidine 
• 53337-88-5 2-methoxy-1-β-D-ribofuranosyl-pyrimidine-4-one 

Downstream Products

• 163496-06-8 5’-O-dimetoxytrityl-2-thiouridine 
• 1627601-87-9 5'-O-dimethoxytrityl-S-geranyl-2-thiouridine 
• 1384570-83-5 5'-O-dimetoxytrityl-2-selenouridine 
• 3413-66-9 α-deoxyadenosine 
• 452-51-7 D-2-deoxyribose 
• 141-90-2 2-thiouracil 
• 6984-55-0 2',3'-O-isopropylidene-2-thiouridine 
• 58479-71-3 5-hydroxymethyl-2',3'-O-isopropylidene-2-thiouridine 
• 21052-20-0 1-(β-D-ribofuranosyl)-4-pyrimidinone 
• 58-96-8 uridine 
• 302918-82-7 3-Benzoyl-1-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-methoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 302918-81-6 3-Benzoyl-1-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 113886-72-9 1-(2-O-methyl-β-D-ribofuranosyl)-2-thio-4-(1H,3H)-pyrimidinone 
• 35763-29-2 2-thio UTP 

Relevant articles and documents

Efficient assessment of modified nucleoside stability under conditions of automated oligonucleotide synthesis: Characterization of the oxidation and oxidative desulfurization of 2-thiouridine

In order to efficiently assess the chemical stability of modified nucleosides to the reagents and conditions of automated oligonucleotide synthesis, we designed, developed and tested a scheme in which the modified nucleoside, directly attached to a solid support, is exposed to the cyclic chemistry of the instrument. Stability of 2-thiouridine against different oxidizers was investigated. Tertbutyl hydroperoxide (1 M) in anhydrous acetonitrile was a more effective oxidizer for the incorporation of 2-thiouridine into oligonucleotide chains than the same oxidizer in methylene chloride. Carbon tetrachloride/water in the presence of a basic catalyst was superior in maintaining the thiocarbonyl function, but its utility for RNA synthesis has yet to be fully tested, whereas 2-phenylsulfonyloxaziridine was a very efficient reagent for oxidative desulfurization of 2-thiouridine.

Reactions of Alkoxyuridines with Ammonia (l)

2-Alkoxy- and 4-alkoxyuridines were converted into isocytidine and cytidine by reaction with ammonia at room temperature.Reaction with hydrogen sulfide produced 2-thio- and 4-thiouridine but the reaction was incomplete.The reaction may be helpful in the identification of alkylated pyrimidine nucleosides in DNA.