154665-03-9Relevant academic research and scientific papers
Osmium-Mediated Transformation of 4-Thiouridine to Cytidine as Key To Study RNA Dynamics by Sequencing
Riml, Christian,Amort, Thomas,Rieder, Dietmar,Gasser, Catherina,Lusser, Alexandra,Micura, Ronald
, p. 13479 - 13483 (2017/10/07)
To understand the functional roles of RNA in the cell, it is essential to elucidate the dynamics of their production, processing and decay. A recent method for assessing mRNA dynamics is metabolic labeling with 4-thiouridine (4sU), followed by thio-select
Synthesis of 4-Thiouridine, 6-Thioinosine, and 6-Thioguanosine 3′,5′-O-Bisphosphates as Donor Molecules for RNA Ligation and Their Application to the Synthesis of Photoactivatable TMG-Capped U1 snRNA Fragments
Kadokura, Michinori,Wada, Takeshi,Seio, Kohji,Sekine, Mitsuo
, p. 5104 - 5113 (2007/10/03)
4-Thiouridine, 6-thioguanosine, and 6-thioinosine 3′,5′-bisphosphates (9, 20, and 28) were synthesized in good yields by considerably improved methods. In the former two compounds, uridine and 2-N-phenylacetylguanosine were converted via transient O-trimethylsilylation to the corresponding 4- and 6-O-benzenesulfonyl intermediates (2 and 13), which, in turn, were allowed to react with 2-cyanoethanethiol in the presence of N-methylpyrrolidine to give 4-thiouridine (3) and 2-N-phenylacetyl-6-thioguanosine derivatives (14), respectively. In situ dimethoxytritylation of these thionucleoside derivatives gave the 5′-masked products 4 and 15 in high overall yields from 1 and 11. 6-S-(2-Cyanoethyl)-5′-O-(4,4′-dimethoxytrityl)-6-thioinosine (23) was synthesized via substitution of the 5′-O-tritylated 6-chloropurine riboside derivative 22 with 2-cyanoethanethiol. These S-(2-cyanoethyl)thionucleosides were converted to the 2′-O-(tert-butyldimethylsilyl)ribonucleoside 3′-phosphoramidite derivatives 7, 18, and 26 or 3′,5′-bisphosphate derivatives 8, 19, and 27. Treatment of 8, 19, and 27 with DBU gave thionucleoside 3′,5′-bisphosphate derivatives 9, 20, and 28, which were found to be substrates of T4 RNA ligase. These thionucleoside 3′,5′-bisphosphates were examined as donors for ligation with m32,2,7 G5′ pppAmUmA, i.e., the 5′-terminal tetranucleotide fragment of U1 snRNA. The 4-thiouridine 3′,5′-bisphosphate derivative 9 was found to serve as the most active substrate of T4 RNA ligase with a reaction efficiency of 96%.
Synthesis of Uridine Analogues to Probe the Functional Group Requirements of the Hairpin Ribozyme
Vyle, Joseph S.,Young, Karen J.,Jones, Sarah,Grasby, Jane A.
, p. S280 - S282 (2007/10/03)
O4-Methyluridine, O2-methyluridine and 4Huridine phosphoramidites were prepared with 2'-O-silyl protection.The methyl modified pyrimidines were synthesised from uridine via the triazolide (O4-methyl) or 2,5'-cyclo derivative (O2-methyl).An improved synthesis of protected 4-thiouridine was also performed.
A convenient synthesis of S-cyanoethyl-protected 4-thiouridine and its incorporation into oligoribonucleotides
Adams, Chris J.,Murray, James B.,Arnold, John R. P.,Stockley, Peter G.
, p. 765 - 768 (2007/10/02)
A reliable preparation of S4-cyanoethyl-4-thiouridine and its incorporation into oligoribonucleotides is reported. Deprotection of oligoribonucleotides with DBU in acetonitrile followed by methanolic ammonia allows the use of standard N-benzyl
