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M8012

Sigma-Aldrich

5-Methyl-2-thiouridine

Synonym(s):

m5s2U

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About This Item

Empirical Formula (Hill Notation):
C10H14N2O5S
CAS Number:
32738-09-3
Molecular Weight:
274.29
EC Number:
251-185-1
MDL number:
MFCD00006556
UNSPSC Code:
41106305
PubChem Substance ID:
24897212

storage temp.

−20°C

SMILES string

CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=S)NC1=O

InChI

1S/C10H14N2O5S/c1-4-2-12(10(18)11-8(4)16)9-7(15)6(14)5(3-13)17-9/h2,5-7,9,13-15H,3H2,1H3,(H,11,16,18)/t5-,6-,7-,9-/m1/s1

InChI key

SNNBPMAXGYBMHM-JXOAFFINSA-N

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Application

5-Methyl-2-thiouridine (m5s2U) is a modified base found in the tRNA of certain extreme thermophiles. 5-Methyl-2-thiouridine may be used to study the physical chemical properties that confer high stability to tRNA and other nucleic acid structures.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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S Patwardhan et al.
Journal of bacteriology, 162(1), 55-60 (1985-04-01)
35S incorporation studies showed that Candida tropicalis tRNA contained two thionucleosides, one of which was identified as 5-methyl-2-thiouridine. The other thionucleoside was alkali labile, and it appeared to be an ester. Pulse-chase experiments suggested that the two thionucleosides were structurally
K Watanabe et al.
Nucleic acids research, 3(7), 1703-1713 (1976-07-01)
5-Methyl-2-thiouridine (S) in tRNA-Met-f from an extreme thermophile is located in the TpsiC region, replacing T, and has a positive CD band centered at 310 nm. Upon heating, the profiles of the change in this band were similar to the
Reactions of 2-thioribothymidine ad 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism.
K Watanabe
Biochemistry, 19(24), 5542-5549 (1980-11-25)
Y Yamamoto et al.
FEBS letters, 157(1), 95-99 (1983-06-27)
1H-NMR analyses have been made on the conformations of 2-thioribothymidine (s2T), 2-thiodeoxyribothymidine (s2dT), as well as ribothymidine (T) and deoxyribothymidine (dT). s2T and s2dT exclusively take the anti form rather than the syn form. The C3'-endo-gg form of the sugar
Benjamin Diop-Frimpong et al.
Nucleic acids research, 33(16), 5297-5307 (2005-09-20)
Substitution of oxygen atoms by sulfur at various locations in the nucleic acid framework has led to analogs such as the DNA phosphorothioates and 4'-thio RNA. The phosphorothioates are excellent mimics of DNA, exhibit increased resistance to nuclease degradation compared
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