Synthesis of Pseudouridine

The Chemistry of Pseudouridine. III. The Structure of the Isomers*

“…These data combined with previous information (Cohn, 1960;Shapiro and Chambers, 1961 , 1963) conclusively establish the structure of pseudouridine AF as 5-~-ribopyranosyluracil. A similar series of reactions establishes the same structure for pseudouridine-AS (see under Experimental).…”

“…40 paper by the descending method. The appropriate RF values are given in Table I. Ion-exchange chromatography and other procedures were carried out as described previously (Shapiro and Chambers, 1961;Chambers et al, 1963). …”

Preparation of Carbocyclic C‐Nucleosides from α‐Chlorooxime Precursor

“…General methods for the synthesis of C-nucleosides include the addition of an organometallic reagent to a ribonolactone derivative followed by hemiacetal deoxygenation, [17] the direct introduction of a preformed heterocyclic base into the anomeric position of a carbohydrate, [18] a Pd 0 -mediated coupling reaction, [19] or the construction of the heterocyclic ring from C-glycosyl derivatives (e.g., nitrile, thioamide, cyanomethoxyacrylonitrile). Recently, Wamhoff et al proposed a novel synthetic approach to purine-like Cnucleosides from C-glycosidic tosyloximino nitrile precursors.…”

Methods for Automatic Nucleotide-Sequence Analysis. Multicomponent Spectrophotometric Analysis of Mixtures of Nucleic Acid Components by a Least-Squares Procedure

“…Nucleosides in 0-01 N-HCI: adenosine, 14-6 x 103 at 257 mpt (Beaven, Holiday & Johnson, 1955); uridine, 10-1 x 103 at 262 m,t (Fox & Shugar, 1952); cytidine, 13-4 x 103 at 280 m,u (Fox & Shugar, 1952); guanosine, 12-2 x 103 at 256-5 mH (Beaven et al 1955); pseudouridine, 7-9 x 103 at 262 mlt (Shapiro & Chambers, 1961). Nucleosides at pH 12-0: adenosine, 14-9 x 103 at 259-5 m,t (Beaven et al 1955); uridine, 7-45 x 103 at 262 m,u (Fox & Shugar, 1952); guanosine, 11-3 x 103 at 264 m,u (Beaven et al 1955); cytidine, 9.1 x 103 at 271 mp (Fox & Shugar, 1952); pseudouridine, 7-8 x 103 at 286 m,u (Michelson & Cohn, 1962); thymine riboside, 11 8 x 103 at 268 m,u (Littlefield & Dunn, 1958); 6-methylaminopurine riboside, 19 7 x 103 at 266 m,u (Littlefield & Dunn.…”