期刊名称：Proceedings of the National Academy of Sciences
印刷版ISSN：0027-8424
电子版ISSN：1091-6490
出版年度：1970
卷号：67
期号：1
页码：93-98
DOI：10.1073/pnas.67.1.93
语种：English
出版社：The National Academy of Sciences of the United States of America
摘要：The use of diethyl pyrocarbonate as a nuclease inhibitor in the preparation of RNA of high molecular weight has prompted a study of the possible reactions of this compound with nucleic acid components under the conditions generally employed for providing inhibition. The first substrate investigated was adenine, which has been found to undergo ring opening with the formation of 5(4)-N-carbethoxyaminoimidazole-4(5)-N'- carbethoxycarboxamidine (II). This product was converted efficiently to isoguanine by treatment with ammonia. The structure of II was established by spectroscopy. For comparisons of reactivity and of spectroscopic and chromatographic properties with the adenine-diethyl pyrocarbonate product, the compounds 9-carbethoxyadenine, 6-N-carbethoxyaminopurine (V), and 6-ethylaminopurine were made; compound V was made by employing the 1-ethoxyethyl protecting group in the synthetic sequence. Purine compounds can be converted to 9-(1-ethoxyethyl) derivatives simply by refluxing in acetal. The facile reaction of adenine with diethyl pyrocarbonate illustrates the importance of gaining information as to the fate of various nucleic acid components in the presence of diethyl pyrocarbonate.
