Some synthetic analogues of uridine diphosphate glucose

Structure−Activity Relationship of Uridine 5‘-Diphosphoglucose Analogues as Agonists of the Human P2Y14 Receptor

“…Replacement of the ribose ring with a 2′-deoxy (S)-methanocarba bicyclic ring 24 (12) also was performed. The uracil ring was modified at the 2 and 4 positions, with the synthesis of 4-thiouridine-5′-diphosphoglucose (13) and 2-thiouridine-5′-diphosphoglucose (15), 25 and at the 5 position, with iodide (16) and fluoride (24). Sugar-modified compounds (25)(26)(27) were synthesized with commercially available sugar monophosphates.…”

“…The uracil ring was modified at the 2 and 4 positions, with the synthesis of 4-thiouridine-5′-diphosphoglucose (13) and 2-thiouridine-5′-diphosphoglucose (15), 25 and at the 5 position, with iodide (16) and fluoride (24). Sugar-modified compounds (25)(26)(27) were synthesized with commercially available sugar monophosphates. Dinucleotides (29) were obtained as byproducts during the synthesis of UDPG analogues and of CDP-glucose 19.…”

Locating 4-thiouridylate in the primary structure of transfer ribonucleic acids

“…The difference between these two spectra was a spectrum characteristic of 4-thioUMP, i.e., it was symmetrical and gaussian between 300 and 360 mg, with a maximum at 332 mg equal to 1.75 % of ß of the Mg 2+-containing undigested tRNA. Using the extinction coefficient e33i = 21.5 X 103 (determined at pH 6.5 for 4-thiouridine (Kochetkov et a!., 1963)) this absorption difference is equivalent to 0.45 mole of 4-thioU/mole of tRNA.…”

Conversion of 4‐thiouridine residues in tRNA into radioactive N‐4‐methylcytidine for sequence analysis

“…Previous reaction conditions for the formation of cytidine by Os04 and NH3 were used [3] except that NH3 was replaced by lower concentrations of methylamine hydrochloride buffers. The product was characterized by paper chromatography and UV spectrophotometry and yields were about 80% based on e33 1 = 2.1 X 104 for 4-thiouridine [8,9]. Unprotonated CH3NH2 is like NH3 in forming a complex with 0s04 which is an active oxidising agent.…”