Cytidine 5 - , sodium

C9HUN307P- Na+ 2 H20 Cytidine (sodium 2, 3 -phosphate), dihydrate CYTCYP20 43 357... 

C19H22N7Na013P 8H20 Guanylyl-(3 — 5 )-cytidine, sodium salt,... 

SynChropak CATSEC columns are evaluated similarly using a polyvinyl-pyridine standard of molecular weight 600,000 and cytidine. The mobile phase is 0.1 % trifluoroacetic (TEA) acid containing 0.2 M sodium chloride. Minimum plate counts are listed in Table 10.4. 

Sodium uridine-5 -phosphate 224 is converted by HMDS 2/TCS 14 and pyrroh-dine at 145 °C, via the assumed persilylated intermediate 225, and after transsilyla-tion with boiling methanol and addition of NaOH, crystalline sodium-cytidine-5 -phosphate 226 in 69% yield [49] (Scheme 4.19). 

C9H11N307P-,Na+,2 H20 Sodium cytidine 2, 3 -cyclic phosphate, dihydrate (CYTCYP20)285... 

C14H25N4OuP2 Na+ 4 H20 Cytidine 5 -(choline diphosphate), sodium salt, tetrahydrate (CYPCHOOl)304... 

Complete confirmation of the structures assigned to the ribonucleosides has been provided by a study of their 5-0- p -tolylsulfonyl derivatives. Whereas 2,3-O-isopropylideneuridine and 2,3-O-isopropylideneinosine give 5-p-tolylsulfonyl derivatives which, with sodium iodide, are converted to 5-deoxy-5-iodo compounds,30 31 the corresponding adenosine and cytidine... 

Catalytic reduction of cytidine in water over rhodium on alumina yields the tetrahydro derivative [l-(/3-D-ribofuranosyl)-4-aminotetrahydropyrimidin-2(l//)-one] and l-( 3-D-ribofuranosyl)tetrahydropyrimidin-2(l/0-one as the major products [680]. The former hydrolyses readily to give tetrahydrouridine,which is a potent inhibitor of human liver deaminase. The latter compound is also formed by sodium borohydride reduction of 5,6-dihydrouridine. 

The structure shown was confirmed by the identification of cytidine 5 -phosphate and N-acetylneuraminic acid after mild acidic hydrolysis, and by the stability of the derivative on treatment with sodium borohydride. Comparison of the optical rotation of the starting derivative182 (44), the products of its hydrolysis,182 and the anomeric... 

In related reactions, Rammler and Khorana reported150 that metha-nolysis ofN4-benzoy]-2, 3, 5 -tri-0-benzoylcytidine in methanol-oxo-lane containing sodium methoxide gaveN4-benzoyl-5 -0-benzoyl-,N4-benzoyl-3, 5 -di-0-benzoyl-, and N4-benzoyl-cytidine. NoN4-benzoyl-2, 5 -di-0-benzoyl derivative was found, presumably as a consequence of benzoyl migration1 from 0-2 to 0-3. ... 

Although the 2, 3 -cyclic phosphates of adenosine, cytidine, guano-sine, and uridine appear to be stable in aqueous solution between, approximately, pH 4 and 9, they are hydrolyzed under more-strenuous conditions (for example, 0.1M hydrochloric acid for 1 hour at room temperature or 0.5 M sodium hydroxide for 12 hours at 37°) to give a mixture of 2 - and 3 -phosphates287 in approximately equal amounts. An appreciation of this aspect of the chemistry of cyclic phosphates was of considerable importance in elucidating the mechanism of the chemical degradation of ribonucleic acid.288... 

The 5,6-double bond in uracil, 5-fluorouracil, /V-alkyluracils, thiouracils, and uridines adds sodium sulfite or bisulfite to give the corresponding 5,6-dihydro-6-sulfonic acid salts. Bisulfite addition to cytosines and cytidine may be succeeded by a second reaction involving nucleophilic replacement of the amino group, for example, by water. 

Early infrared (IR) spectroscopy studies were inconclusive some37 38 were considered to indicate that cytosine exists in the amine-lactim form (1) in the solid state, others39-41 that it exists in the amine-lactam form (2 or 3). More recent studies42-50 (for reviews, see refs. 51, 52) on cytidine, 5-halodeoxycytidines, sodium cytidylate, and polycytidylic acid in neutral H20 or D20 solution advocate, however, the structure 2 for the cytosine residue. 

Mixtures of photolabile 2 - and 3 -0-(2-nitrobenzyl)ribonucleosides were obtained in good yields when adenosine, uridine, cytidine, and inosine were treated with 2-nitrophenyldiazomethane in the presence of tin(II)chloride [362]. The dibutylstan-nylene approach has been used for the preparation of 2 -(4-nitrobenzyl)uridine [366]. 2-Nitrobenzyl chloride and sodium hydride in DMF gave the 2 -ethers in 26-37% yield, depending on the starting nucleoside [363, 367]. 

Purine and pyrimidine bases and their nucleosides (adenosine, adenine, cytidine, cytosine, guanosine, guanine, inosine, thymine, uridine, uracil) ODSS (octadecyl sulfonated silica), 10 pm Acetonitrile . 8 mM sodium acetate, pH 4.5 (40 60) 270 mm x 20.5 pm i.d 205 mm effective lengtl... 

Rosenberg JM, Seeman NC, Day RO, Rich A (1976) RNA double-helical fragment at atomic resolution. II. The crystal structure of sodium guanylyl-3, 5 -cytidine monohydrate. J Mol Biol 104 145-167... 

Synthetic cytidine ribitol pyrophosphate was prepared by condensing cytidine 5-phosphate and D-ribose 5-phosphate in the presence of dicyclohexylcarbodiimide, followed by the reduction of the cytidine D-ribose pyrophosphate with sodium borohydride. 

Fig. 2. The dependence of nucleoside-protein conjugation on pH. A mixture of periodate-oxidized adenosine and cytidine was added to bovine y-globulin to give final concentrations of 4 mM nucleoside (0.9 mg/ml) and 6.7 ftM protein (1 mg/ml) in 0.2 M Veronal buffer titrated to varying pH. These mixtures were incubated at room temperature for 1.5 hr. Then sodium borohydride was added to a final concentration of 0.4 M (15 mg/ml), and samples were incubated for 2.5 hr at 4°. They were then dialyzed extensively against 0.1 M NaCl and analyzed for protein and nucleoside composition.

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