Biosynthesis of 2'-deoxycoformycin: evidence for ring expansion of the adenine moiety of adenosine to a tetrahydroimidazo[4,5-d][1,3]diazepine system.
Biosynthesis of 2'-deoxycoformycin: evidence for ring expansion of the adenine moiety of adenosine to a tetrahydroimidazo[4,5-d][1,3]diazepine system.
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DOI：
10.1021/bi00392a008
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发表时间：
1987-09
期刊：
影响因子：
2.9
通讯作者：
J. Hanvey;E. Hawkins;J. Tunac;J. J. Dechter-J.;D. Baker;R. Suhadolnik
中科院分区：
文献类型：
--
作者：
J. Hanvey;E. Hawkins;J. Tunac;J. J. Dechter-J.;D. Baker;R. Suhadolnik
2‘-脱氧辅霉素(2’-DCF)是抗菌链霉菌产生的一种微量的核苷类抗肿瘤药物，早期研究表明它来源于腺苷完整的碳-氮结构。使用13C和二维傅立叶变换核磁共振技术的其他实验，结合放射性标记研究，确定D-核糖的C-1，而不是四氢叶酸的“C-1池”，是2‘-DCF的配基中C-7碳的来源。这些结果表明，腺苷的腺嘌呤部分(或其核苷酸)经历了独特的扩环，在腺嘌呤环的N-1和C-6之间插入一个-CH2-单元，以提供2‘-DCF的1，3-二氮卓部分。
2'-Deoxycoformycin (2'-dCF), a nucleoside antitumor agent produced in trace quantities by Streptomyces antibioticus, has been shown in earlier work to originate from the intact carbon-nitrogen framework of adenosine. Additional experiments using 13C and two-dimensional Fourier transform NMR techniques, together with radiolabeling studies, identify the C-1 of D-ribose, and not the tetrahydrofolate "C-1 pool", as the source of the C-7 carbon in the aglycon of 2'-dCF. These results show that the adenine portion of adenosine (or a nucleotide thereof) undergoes a unique ring expansion, by insertion of a -CH2- unit between the N-1 and C-6 of the adenine ring, to furnish the 1,3-diazepine portion of 2'-dCF.