REACTION OF FORMALDEHYDE WITH NUCLEOTIDES AND RIBONUCLEIC ACID
REACTION OF FORMALDEHYDE WITH NUCLEOTIDES AND RIBONUCLEIC ACID
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DOI：
10.1016/0005-2787(67)90687-9
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发表时间：
1967-01-01
期刊：
影响因子：
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通讯作者：
FELDMAN, MY
中科院分区：
文献类型：
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作者：
FELDMAN, MY
The products of formaldehyde condensation with purine nucleotides and RNA were separated and isolated chromatographically. Adenylic acid, like adenine and adenosine, affords a methylene bis-derivative on treatment with formaldehyde. Three isomers of methylene bis-(adeno-sine 2[image](3[image])-phosphate) were separated by chromatography on Dowex I (formate); the isomers differ from each other in the positions of the phosphate residues. On enzymic dephosphorylation, all 3 isomers produced a compound identified chromatographically and spectrophoto-metrically as methylene bis-adenosine. The reaction of nucleotides with formaldehyde yield, besides adenylic methylene dinucleotide, guanylic methylene dinucleotide and methylene adenine-guanine dinucleotide. The latter compounds were identified kinetically by the bell-shaped curve of the dependence of the product formation rate upon the logarithm of formaldehyde concentration, peculiar to methylene bis-derivatives. Other indirect evidence for the formation of methylene bis-guanylic acid and methylene adenine-guanine dinucleotide was also obtained. No condensation products of pyrimidine nucleotides with formaldehyde have been detected by chromatography. All 3 above-mentioned methylene dinucleotides (P-Ado-CH2-Ado-P,P-Guo-CH2-Guo-P and P-Ado-CH2-Guo-P) were isolated from the alkaline hydrolysate of formaldehyde-treated RNA. No indications of the formation of bridges between pyrimidine residues of RNA were obtained. A method for the quantitative estimation of methylene derivatives in formaldehyde-treated RNA was developed. At pH 4.8 and 20[degree] the reaction of RNA and formaldehyde is complete in about 15 days; at a low ionic strength, from 15-19% of the purine bases of RNA form methylene dimers. When treated with formaldehyde under similar conditions RNA was found to contain twice as many bridges as are present in the mixture of purine nucleotides. The possibility of the intramolecular formation of cross-links in RNA and their use in biochemical investigations and for the interpretation of certain biological effects of formaldehyde is discussed.
