Adenosine periodate oxidation

Jervis used porous silica coated with chemisorbed polyacrylhydrazide for immobilization of adenosine monophosphate (AMP) [117]. After periodate oxidation of its ribose residue the ligand was coupled to the carrier and used for isolation of lactate dehydrogenase from rabbit muscle. The specific capacity was 2 mg of protein/g adsorbent with a ligand content of 10 pmol/g, whereas recovery of enzymatic activity after elution was 85%. Hipwell et al. [118] found that for effective binding of lactate dehydrogenases on AMP-o-aminoalkyl-Sepharose the spacer arm length required at least 4 methylene links. Apparently, a macromolecule of polyacrylhydrazide acts itself like an extended spacer arm and thus allow AMP to bind the enzyme. 

A method has been developed which is designed to remove nucleotide residues singly from a polynucleotide chain, and it is anticipated that more precise information will shortly be forthcoming regarding the order in which the nucleotides are linked.220 The method is based on the fact that esters of 3-oxo alcohols are unstable toward alkali. In agreement with this, it is found that the products of the action of periodate on adenosine 5-phosphate (XXX) or adenosine 5-(benzyl hydrogen phosphate) are hydrolyzed under very mild conditions. Thus, after removal of terminal, singly-esterified phosphoryl residues from a polynucleotide chain, it is anticipated that periodate oxidation and hydrolysis will result in the removal of the... 

Periodic acid oxidation has proved to be a very useful tool in enzymology since a wide variety of biochemicals contain hydroxyl groups on adjacent carbon atoms. For example, periodate-oxidized ATP (also called adenosine 5 -triphosphate 2, 3 -dialdehyde) has often been used as an alternative substrate or an irreversible inhibitor for a wide variety of ATP-utilizing enzymes. This compound, and many others, are now commercially available, even though they are readily synthesized e.g., periodic acid oxidized ADP, AMP, adenosine, P, P -di(adenosine-5 )pentaphosphate, P, P -di(adenosine-5 )tetraphos-phate, GTP, GDP, GMP, guanosine, CTP, CDP, CMP, etc. In the case of the nucleosides, commercial sources also can supply the dialcohol form of the nucleoside i.e., the nucleoside has first been oxidized with periodic acid and then reduced to the dialcohol with borohydride. 

Adenosine 5 -triphosphate-2, 3 -dialdehyde, MALAPRADE REACTION (PERIODATE OXIDATION)... 

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.

Mild treatment of periodate-oxidized adenosine 5-phosphate or adenosine 5-(benzyl hydrogen phosphate) with alkali gave adenine and inorganic phosphate or benzyl phosphate. " " Periodate oxidation followed by alkali treatment would, therefore, be a means of degrading polynucleotides step-wise. " " A dinucleotide has been degraded in this way. " ... 

Adenosine triphosphate, when oxidized to its dialdehyde with periodate and condensed with Sepharose-adipic (or sebacic) acid hydrazide, has been used to isolate poly(A) polymerase, and also myosin and its fragments from different sources. A poly(A)-linked resin has been prepared by condensing 4,4 -diaminodiphenyl-methane with periodate-oxidized starch, reducing the resulting Schiff bases with borohydride, diazotizing, and then coupling with the polynucleotide. The resulting material may be used to isolate poly(U) sequences. 

Hoffman J. Murine erythroleukemia cells resistant to periodate-oxidized adenosine have lowered levels of nucleoside transporter. Adv Exp Med Biol 1991 309A 443 46. 

Acetamido-2-deoxy-D-galactono-l,4-Iactone 2-Acetamido-2-deoxy-D-glucono-1,4-lactone 2-Acetamido-2-deoxy-D-mannono-l,4-lactone Adenosine 5 -triphosphate (periodate-oxidized)... 

Studies in experimental species demonstrate that methyl donor availability affects the methylation of iAs. In mice exposed to arsenite (As ), depletion of the intracellular pool of 5-adomet by treatment with periodate-oxidized adenosine (PAD), an inhibitor of 5-adomet synthesis (Hoffman 1980), results in reduced urinary excretion of DMA (Marafante and Vahter 1984). Marafante and Vahter (1986) showed that consumption of choline-deficient diet decreased the urinary excretion of DMA and increased tissue As retention in rabbits given 0.4mg arsenate (As )/kg i.v. The same effect of a diet deficient in choline, methionine, and protein was observed in rabbits after administration of 0.4mg As Vkg i.v. (Vahter and Marafante 1987). 

On oxidation with periodic acid, nucleosides which contain a n-ribofuran-osyl group, for example, adenosine, yield a monoformazan derivative ... 

Irreversible inhibition of ADP and CDP reduction in Ehrlich tumor cells was caused by ATP-, AMP- or adenosine oxidized with sodium periodate. The inhibition probably involves Schiff base formation between the 2, 3 -dialdehyde product and a lysine residue(s), because pyridoxal phosphate also inhibits ADP and CDP reduction (141, 142). 

Eibonucleoside 5 -phosphates possess an unsubstituted, vicinal cis-glycol system. Such systems complex with boric acid, and an increase in the acidity results. In addition, these a-m-glycol systems are cleaved by metaperiodate to their corresponding dialdehydes. Thus, adenosine 5 -phosphate consumes one mole of periodate per mole, whereas yeast adenylic acid (the 2 - and 3 -monophosphates of adenosine see p. 312) is resistant to this oxidant. ... 

Various nucleoside dialdehydes, obtained by periodate cleavage, have been tested for antitumour activity. The periodate forms of strongly basic anion exchangers have been used for the selective oxidation of ribofuranosyl nucleosides in the presence of galacto- and gluco-pyranosides. Routes have been developed for the regioselective synthesis of both adenosine monoaldehydes the previously-unknown 3 -monoaldehyde 266 was made from the dialdehyde by selective protection of the 3 -aldehyde as the JV,A -diphenylimidazolidine derivative, followed by borohydride reduction. ... 

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