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2-Thiouridine

CAS No.:
20235-78-3
Catalog Number:
AG002875
Molecular Formula:
C9H12N2O5S
Molecular Weight:
260.2670
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25mg
98%(HPLC)
In Stock USA
United States
$87
- +
50mg
98%(HPLC)
In Stock USA
United States
$144
- +
100mg
98%(HPLC)
In Stock USA
United States
$241
- +
250mg
98%(HPLC)
In Stock USA
United States
$519
- +
500mg
98%(HPLC)
In Stock USA
United States
$832
- +
Product Description
Catalog Number:
AG002875
Chemical Name:
2-Thiouridine
CAS Number:
20235-78-3
Molecular Formula:
C9H12N2O5S
Molecular Weight:
260.2670
MDL Number:
MFCD03788697
IUPAC Name:
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-sulfanylidenepyrimidin-4-one
InChI:
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
InChI Key:
GJTBSTBJLVYKAU-XVFCMESISA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(=O)[nH]c1=S
Properties
Complexity:
374  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
260.047g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
260.264g/mol
Monoisotopic Mass:
260.047g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
134A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.4  
Literature
Title Journal
Prediction of the stability of modified RNA duplexes based on deformability analysis: oligoribonucleotide derivatives modified with 2'-O-cyanoethyl-5-propynyl-2-thiouridine as a promising component. Chemical communications (Cambridge, England) 20120725
Crystal structures of murine norovirus-1 RNA-dependent RNA polymerase in complex with 2-thiouridine or ribavirin. Virology 20120510
Identification of novel N-(morpholine-4-carbonyloxy) amidine compounds as potent inhibitors against hepatitis C virus replication. Antimicrobial agents and chemotherapy 20120301
The 2-thiouridine unit in the RNA strand is desulfured predominantly to 4-pyrimidinone nucleoside under in vitro oxidative stress conditions. Chemical communications (Cambridge, England) 20110507
Human mitochondrial tRNAs: biogenesis, function, structural aspects, and diseases. Annual review of genetics 20110101
A forward-genetic screen and dynamic analysis of lambda phage host-dependencies reveals an extensive interaction network and a new anti-viral strategy. PLoS genetics 20100701
[Functions and biosynthesis pathway of sulfur-modifications in tRNA]. Seikagaku. The Journal of Japanese Biochemical Society 20100701
Theoretical study on conformational preferences of ribose in 2-thiouridine--the role of the 2'OH group. Physical chemistry chemical physics : PCCP 20100421
Chemical synthesis of LNA-2-thiouridine and its influence on stability and selectivity of oligonucleotide binding to RNA. Biochemistry 20091124
Preparation of short interfering RNA containing the modified nucleosides 2-thiouridine, pseudouridine, or dihydrouridine. Current protocols in nucleic acid chemistry 20090601
Chemical synthesis and properties of 5-taurinomethyluridine and 5-taurinomethyl-2-thiouridine. The Journal of organic chemistry 20090320
Orchestrating sulfur incorporation into RNA. Nature chemical biology 20060401
Structural basis for sulfur relay to RNA mediated by heterohexameric TusBCD complex. Structure (London, England : 1993) 20060201
Facilitating RNA structure prediction with microarrays. Biochemistry 20060117
Structural effects of hypermodified nucleosides in the Escherichia coli and human tRNALys anticodon loop: the effect of nucleosides s2U, mcm5U, mcm5s2U, mnm5s2U, t6A, and ms2t6A. Biochemistry 20050607
MnmA and IscS are required for in vitro 2-thiouridine biosynthesis in Escherichia coli. Biochemistry 20030204
Synthesis and properties of 2'-O-alkylated 2-thiouridine derivatives and oligonucleotides containing 2'-O-alkylated 2-thiouridine derivatives. Nucleic acids research. Supplement (2001) 20030101
Conserved bases in the TPsi C loop of tRNA are determinants for thermophile-specific 2-thiouridylation at position 54. The Journal of biological chemistry 20021018
Accurate translation of the genetic code depends on tRNA modified nucleosides. The Journal of biological chemistry 20020510
Wobble modification defect in tRNA disturbs codon-anticodon interaction in a mitochondrial disease. The EMBO journal 20010903
Efficient assessment of modified nucleoside stability under conditions of automated oligonucleotide synthesis: characterization of the oxidation and oxidative desulfurization of 2-thiouridine. Nucleosides, nucleotides & nucleic acids 20010101
Properties