5618-60-0Relevant academic research and scientific papers
Synthesis and Utility of 5-Thiocyanato Deoxyuridine and Uridine Phosphoramidites as Masked Synthons
Bradley, David H.,Hanna, Michelle M.
, p. 6223 - 6226 (2007/10/02)
5-Thiocyanato-2'-deoxyuridine and 5-thiocyanato-uridine phosphoramidites have been synthesized and incorporated into DNA and RNA trimers via automated methodology.The SCN group has been removed with DTT treatment, and a photocrosslinking aryl azide has be
Synthesis, chemistry, and biological activity of 5 thiocyanatopyrimidine nucleosides as potential masked thiols
Nagamachi,Fourrey,Torrence,Waters,Witkop
, p. 403 - 406 (2007/10/09)
The reaction of chlorothiocyanogen (ClSCN) with various derivatives of uracil was investigated as potential route to 5 mercaptouracils. Reaction of 1,3 dimethyluracil, 1 (β D ribofuranosyl)uracil, 1 (2' deoxy β D ribofuranosyl)uracil, 1 (β D arabinofuranosyl)uracil, 1 (2',3',5' tri O chloroacetyl β D ribofuranosyl)uracil, and 1 (2',3',5' tri O acetyl β D ribofuranosyl)uracil with ClSCN in acetic acid gave the corresponding 5 thiocyanato derivatives in fair to excellent yields. These 5 thiocyanatopyrimidine nucleosides can be reduced by dithiothreitol, sodium dithionite 2 mercaptoethanol, or glutathione to the biologically active 5 mercaptopyrimidine nucleosides. The intermediate 5 thiocyanatopyrimidine nucleosides show significant biological activity, probably as the result of in vivo reduction.
