The Pathway of Decomposition of Myoadenylic Acid During Autolysis in Various Tissues

Kerr, Stanley E.; Seraidarian, Krikor

doi:10.1016/s0021-9258(17)41571-7

Cited by 10 publications

(1 citation statement)

References 15 publications

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“…Under standard conditions (6 n HC1, 20 min, 100°), 2'-O-methyladenosine gave a color yield that was 23% that of adenosine; 3'-O-methyladenosine, 100%; 5'-O-methyladenosine, 125%; and 2',3'-di-0-methyladenosine, 15%. 5'-Adenylic acid gave 138% of the color produced by adenosine in agreement with earlier results (Kerr and Seraidarian, 1945;Albaum and Umbreit, 1947), and AxpAp, an O-methyl-6s TIME OF HEATING AT 100°( Min) figure 5: Color yield of 2'-O-methyladenosine as a function of time of heating in the orcinol reaction. Values are expressed as a percentage of the color yield of an equivalent amount of adenosine under identical conditions.…”

Section: Resultssupporting

confidence: 89%

The preparation and properties of O-methylated adenosine derivatives

Gin¹,

Dekker²

1968

Biochemistry

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By reacting diazomethane with adenosine in a partially aqueous medium, 2'-O-methyladenosine, 3'-O-methyladenosine, 5'-O-methyladenosine, and 2',-3'-di-O-methyladenosine have been prepared in 38, 11, 1.5, and 3.5% yields, respectively. These yields are in general accord with the known mechanism of action of diazomethane and with the acidities of the individual hydroxyl groups of adenosine as determined by ion-exchange chromatography of the O-methylated derivatives on Dowex 1 (OH-) columns, i.e., the more acidic the hydroxyl groups, the greater the extent of methylation. Replacement of the 2'and/or 3'-hydroxyl group of adenosine by a methoxyl group slightly stabilized the glycosyl bond to acid-catalyzed hydrolysis. For 0.1 n HC1, 97.5°, the following first-order rate constants were determined: adenosine, 10 X 10-4 sec-1; 5'-0-^^/hile it is now clearly established that both tand rRNAs are frequently methylated at the 2'-oxygen of some of their ribose residues (Smith and Dunn, 1959; Singh and Lane, 1964a,b;Hall, 1964), our knowledge of the chemical behavior and biological significance of 2'-0-methyl nucleoside residues is, at best, fragmentary.Recent progress in methylating procedures (Broom and Robins, 1965; Khwaja and Robins, 1966) has made possible selective O methylation of adenosine and cytidine. Using the Broom and Robins (1965) procedure which employs diazomethane in aqueous dimethoxyethane, we have obtained on reaction of adenosine: 3'-O-methyladenosine, 5'-O-methyladenosine, and 2',-3'-di-O-methyladenosine in addition to the 2 '-0methyladenosine initially reported (Broom and Robins, 1965). These methylated adenosines can be readily separated by a combination of cellulose and anion-exchange chromatography making use, in the case of the latter technique, of the variation in acidity of the remaining hydroxyl groups of the derivatized adenosines (Dekker, 1965). In this paper we describe the isolation and properties of several methylated adenosines and their behavior toward (1) acid hydrolysis, (2) enzymatic deamination, and (3) the orcinol reaction.The preparation of 3'-O-methyladenosine has also been accomplished by the coupling of the appropriate

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Section: Resultssupporting

confidence: 89%