M8012
5-Methyl-2-thiouridine
Synonym(s):
m5s2U
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About This Item
Empirical Formula (Hill Notation):
C10H14N2O5S
CAS Number:
Molecular Weight:
274.29
UNSPSC Code:
41106305
PubChem Substance ID:
EC Number:
251-185-1
MDL number:
InChI key
SNNBPMAXGYBMHM-JXOAFFINSA-N
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
SMILES string
CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(=S)NC1=O
storage temp.
−20°C
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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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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K Watanabe et al.
Journal of biochemistry, 96(5), 1625-1632 (1984-11-01)
An extreme thermophile, Thermus thermophilus HB 8, contains two types of tRNAs, T- and S2T-containing tRNAs. Their relative content changes depend on the growth temperature of the bacterial cells (1-3). To elucidate the reason why the extreme thermophile possesses the
N Horie et al.
Biochemistry, 24(21), 5711-5715 (1985-10-08)
From Thermus thermophilus HB8 grown at 65 degrees C, two major tRNAIle species have been purified by column chromatography and polyacrylamide gel electrophoresis. The nucleotide sequence of one of these two tRNAIle1 species (tRNAIle1a) has been determined to be pGGGCGAUUAGCUCAGCUGmGUDAGAGCGCACGCCUGAUt6AAGCGUGAGm7GUCGGUGGs2T
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
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