CHARACTERIZATIONS AND SOME CHEMICAL REACTIONS OF PERIODATE-OXIDIZED NUCLEOSIDES

Journal Article · Mon Dec 19 23:00:00 EST 1960 · Journal of the American Chemical Society (U.S.)

DOI:https://doi.org/10.1021/ja01509a046· OSTI ID:4118715

Khym, J X; Cohn, W E

Phenylhydrazine reacts with the periodate oxidation products of adenosine, guanosine, uridine, and cytidine to form bisphenylhy-drazones, which were isolated and characterized. These substances react further with phenylhydrazine to form adenine, guanine, uracil, and cytosine and 2- and 3- carbon fragments. Sodium borohydride reduces both aldehyde groups of the oxidized nucleosides when the reaction is carried out under alkaline conditions, but selective reduction of the aldehyde group distal to the purine or pyrimidine ring occurs under slightly acidic conditions. Ion exchange and paper chromatographic methods were developed for the examination of the dialdehydes and the corresponding reduction products were obtained from them. Evidence is presented indicating that the acid hydrolysis of the completely reduced products. the tri-alcohols, is probably initiated at the glycosidic linkage. A new micro method for measuring and removing periodate and iodate essentially in one step was developed. (auth)

• Research Organization: Oak Ridge National Lab., Tenn.
• Sponsoring Organization: USDOE
• NSA Number: NSA-15-007263
• OSTI ID: 4118715
• Journal Information: Journal of the American Chemical Society (U.S.), Journal Name: Journal of the American Chemical Society (U.S.) Vol. Vol: 82; ISSN JACSA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

ACIDITY
ACIDS
ADENINE
ADENOSINE
ALCOHOLS
ALDEHYDES
BORON HYDRIDES
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
CYTIDINE
CYTOSINE
DRUGS
GUANINE
GUANOSINE
HETEROCYCLICS
HYDRAZINE
HYDRAZONES
HYDROLYSIS
IODATES
IODINE OXIDES
ION EXCHANGE
MEASURED VALUES
NUCLEIC ACIDS
NUCLEOSIDES
ORGANIC NITROGEN COMPOUNDS
OXIDATION
PAPER
PERIODATES
PHENYL RADICALS
PYRIMIDINES
REDUCTION
RIBONUCLEIC ACID
SODIUM HYDRIDES
URACILS
URIDINE
VITAMIN B-4
VITAMINS