113886-72-9

Basic information

• Product Name: 2'-O-methyl-2-thiouridine
• Synonyms: 2'-O-methyl-2-thiouridine
• CAS NO: 113886-72-9
• Molecular Formula: C₁₀H₁₄N₂O₅S
• Molecular Weight: 274.29356
• Mol File: 113886-72-9.mol

Chemical Properties

• Appearance: /
• Density: 1.55±0.1 g/cm3(Predicted)
• PKA: 6.97±0.20(Predicted)
• CAS DataBase Reference: 2'-O-methyl-2-thiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-O-methyl-2-thiouridine(113886-72-9)
• EPA Substance Registry System: 2'-O-methyl-2-thiouridine(113886-72-9)

Safety Data

• Hazardous Substances Data: 113886-72-9(Hazardous Substances Data)

Upstream product

• 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 
• 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 
• 68045-07-8 1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose 
• 2140-76-3 2'-O-methyluridine 
• 1613530-35-0 C₁₁H₁₆N₂O₈S 
• 1352173-49-9 2'-O-Me-2'-O-ethyluridine 
• 75-09-2 dichloromethane 
• 7553-56-2 iodine 
• 302918-80-5 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 
• 155006-24-9 1-(3,5-di-O-benzoyl-2-O-methyl-β-D-ribofuranosyl)-2-thio-4-(1H,3H)-pyrimidinone 
• 20235-78-3 2-thiouridine 

Relevant articles and documents

Alternative nucleic acid molecules and uses thereof

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.

MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF

The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

A New Route to 2′-O-Alkyl-2-thiouridine Derivatives via 4-O-Protection of the Uracil Base and Hybridization Properties of Oligonucleotides Incorporating These Modified Nucleoside Derivatives

Oligonucleotides containing 2-thiouridine (s2U) in place of uridine form stable RNA duplexes with complementary RNAs. Particularly, this modified nucleoside has proved to recognize highly selectively adenosine, the genuine partner, without form

Synthesis and properties of 2'-O-methyl-2-thiouridine and oligoribonucleotides containing 2'-O-methyl-2-thiouridine

A new method for the synthesis of 2'-O-methyl-2-thiouridine (s2Um) found in thermophilic bacterial tRNA was developed. Structural properties of s2Um and s2Um(p)U were studied by using 1H NMR spectroscopy. A modified nonaribonucleotide (RNA*: 5'-CGUUs2UmUUGC-3') was synthesized to study the base-recognition ability of s2Um in formation of RNA-RNA and RNA-DNA duplexes. The UV melting experiments revealed that RNA*-RNA and RNA*-DNA duplexes having an s2U-A base pair are more stable than those having a U-A base pair. On the contrary, the thermal stability of RNA*-RNA and RNA*-DNA duplexes having an s2U-G wobble base pair was much lower than that of the unmodified duplexes having a natural U-G base pair. It is concluded that s2Um has higher selectivity toward A over G than unmodified U. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis of novel C-2 substituted pyrimidine nucleoside analogs

A series of 2-(2-oxoalkylidene)-4(1H)-pyrimidinone nucleoside analogs were synthesized by the addition of the lithium enolates of methylketones to 2,5'- and 2,2'-anhydrouridines and to 2,5'-anhydrothymidines. Alternatively, 2- thiouridine was alkylated with bromomethyl ketones to yield 2-(2- oxoalkyl)thio-4(1H)-pyrimidinone ribofuranosides in good yields. These intermediates were subsequently transformed into the title compounds via an Eschenmoser sulfur extrusion reaction. The 2-(2-oxoalkylidene)-4-(1H)- pyrimidinone nucleoside analogs exhibit enol proton signals in their 1H nmr spectra indicative of hydrogen bonding between N-3 and keto oxygen. These structures offer functional groups with potential for Watson-Crick hydrogen bonding.