Studies of Phosphorylation. I. Phosphorylation of 2′, 3′-<i>O</i>-Isopropylidene Nucleoside by Phosphoryl Chloride
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- Masaharu Yoshikawa
- Central Research Laboratories, Ajinomoto Co., Inc
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- Tetsuya Kato
- Central Research Laboratories, Ajinomoto Co., Inc
書誌事項
- タイトル別名
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- Studies of phosphorylation. I. Phosphorylation of 2',3'-o-isopropylidene nucleoside by phosphoryl chloride.
抄録
<jats:title>Abstract</jats:title> <jats:p>5′-Nucleotides could be conveniently prepared in high yields by the phosphorylation of 2′, 3′-O-isopropylidene nucleosides with phosphoryl chloride in the absence of any organic solvent. The rate of phosphorylation in a large excess of phosphoryl chloride was markedly promoted by the partial hydrolysis of phosphoryl chloride with a small amount of water. The undesirable cleavage of the glycosidic linkage in nucleoside, which was observed particularly in a strongly acidic medium caused by the addition of excessive water, could be suppressed by the addition of ethers or amines in a phosphoryl chloride solution. 2′, 3′-O-Isopropylidene derivatives of adenosine, inosine, and guanosine gave the corresponding 5′-nucleotides in good yields, whereas that of xanthosine reacted very slowly, unlike the above nucleosides. All attempts at the phosphorylation of 2′, 3′-O-isopropylidene-2-mercaptoinosine were unsuccessful. The influence of substituents at the 2-position in purine bases on phosphorylation was investigated by comparing the reactivity between the above-mentioned nucleosides and their methylated derivatives, such as 2-dimethylaminoinosine, 2-methoxyinosine, and 2-methylthioinosine; it was found that these methylated nucleosides were readily phosphorylated to give the corresponding 5′-nucleotides in nearly quantitative yields.</jats:p>
収録刊行物
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- Bulletin of the Chemical Society of Japan
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Bulletin of the Chemical Society of Japan 40 (12), 2849-2853, 1967-12-01
Oxford University Press (OUP)