SYNTHESIS OF 5-SUBSTITUTED PYRIMIDINES VIA FORMALDEHYDE ADDITION
SYNTHESIS OF 5-SUBSTITUTED PYRIMIDINES VIA FORMALDEHYDE ADDITION
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DOI：
10.1021/ja01519a056
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发表时间：
1959-01-01
影响因子：
15
通讯作者：
FINK, K
中科院分区：
文献类型：
--
作者：
CLINE, RE;FINK, RM;FINK, K
对5-羟甲基尿嘧啶的合成和性质进行了重新研究，结果表明该化合物不稳定，只需在尿嘧啶上加成甲醛，收率可达80%。5-羟甲基化合物，包括由山茱萸酸、尿嘧啶和脱氧尿嘧啶制备的化合物，被氧化为5-甲酰基和5-羧基嘧啶，氢化为5-甲基、5-羟甲基二氢和5-甲基二氢嘧啶，并与醇和酸（包括氨基酸）缩合。尿嘧啶和尿嘧啶的放射性5-羟甲基衍生物被用于生物学研究。甲醛及其与嘧啶的加成产物是目前与核酸代谢问题有关的相当大的兴趣。Wyatt和Cohen发现5-羟甲基胞嘧啶是T-even噬菌体DNA的独特组成部分，2和Flaks和Cohen注意到噬菌体感染的大肠杆菌含有酶，可以利用甲醛将脱氧胞嘧啶转化为5-羟甲基衍生物，或将脱氧尿酸转化为胸腺嘧啶。弗里德金也用正常大肠杆菌的提取物对后一种转化进行了研究，并发现在胸腺的提取物中，甲醛和脱氧尿苷也会形成类似的胸腺嘧啶。6·6甲醛加成产物
A reinvestigation of the synthesis and properties of 5-hydroxymethyluracil has revealed that this compound is not unstable and can be prepared in 80% yield by the simple addition of formaldehyde to uracil. The 5-hydroxymethyl compounds, including those prepared from orotic acid, uridine and deoxyuridine, were oxidized to 5-formyl-and 5-carboxypyrimidines, hydrogenated to 5-methyl-, 5-hydroxymethyldihydro-and 5-methyldihydropyrimidines and condensed with alcohols and acids (including amino acids). Radioactive5-hydroxymethyl derivatives of uracil and uridine were used in biological studies.Formaldehyde and its addition products with pyrimidines are presently of considerable interest in connection with problems of nucleic acid metabolism. Wyatt and Cohen identified 5-hydroxymethylcytosine as a unique constituent of the DNA of T-even bacteriophage, 2 and Flaks and Cohen noted that phage-infected E. coli contain enzymes which can utilize formaldehyde to convert deoxycytidylic acid to the5-hydroxymethyl derivative, or deoxyuri-dylic acid to thymidylic acid. 3 The latter trans-formation has also been studied by Friedkin using extracts of normal E. coli, 4 and a similar formation of thymidine from formaldehyde and deoxyuridine has been found to occur with extracts of thymus gland. 6· 6 The addition product of formaldehyde