NUCLEOSIDE ANTIBIOTICS .6. BIOSYNTHESIS OF PYRROLOPYRIMIDINE NUCLEOSIDE ANTIBIOTIC TOYOCAMYCIN BY STREPTOMYCES-RIMOSUS
NUCLEOSIDE ANTIBIOTICS .6. BIOSYNTHESIS OF PYRROLOPYRIMIDINE NUCLEOSIDE ANTIBIOTIC TOYOCAMYCIN BY STREPTOMYCES-RIMOSUS
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DOI：
10.1021/bi00807a030
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发表时间：
1970-01-01
期刊：
影响因子：
2.9
通讯作者：
SUHADOLN.RJ
中科院分区：
文献类型：
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作者：
UEMATSU, T;SUHADOLN.RJ
摘要：研究了链霉菌合成的吡咯嘧啶核侧抗生素toyocamycin。腺嘌呤-2- 14c，而不是腺嘌呤-8- 14c，被纳入到toyocamycin中。从腺嘌呤-2- 14C实验中得到的所有toyocamycin中的14C都位于toyocamycin的C-2中。这可以通过将toyocamycin(1)转化为3-羧基乙基衍生物(5)来证明。toyocamycin的C-2在碱中加热后释放为甲酸。由中间体2-氨基-4-羧基-3-羰基-[lV-（2-羧基乙基）]- 1 -/3- d -核呋喃基吡咯(7)合成的5-羧基-4-羟基-7-（/3- d -核呋喃基）吡咯-[2,3 -c/ j嘧啶(8)]，经甲酸和乙酸酐处理，无放射性。化合物2,3,4,5，I-S在过去的18年中，从细菌和真菌中分离出34种核苷类抗生素，它们具有广泛的化学结构和对病毒、细菌和肿瘤细胞的生物活性（Suhadolnik, 1970）。腺嘌呤和/或腺苷在核苷类抗生素虫草素（3′-脱氧腺苷）、3′-氨基-3′-脱氧腺苷、3′-乙酰氨基-3′-脱氧腺苷、psicofuranine、decoyinine、tubercidin和
T. Uematsu and R. J. Suhadolnikt abstract: The biosynthesis of the pyrrolopyrimidine nucleo-side antibiotic, toyocamycin elaborated by Streptomyces rimosus, has been studied. Adenine-2-14C, but not adenine-8-14C, is incorporated into toyocamycin. All of the 14C in the toyocamycin from the adenine-2-l4C experiments resides in C-2 of toyocamycin. This was shown by the conversion of toyocamycin (1) into the 3-carboxyethyl derivative (5). C-2 of toyocamycin was released as formic acid by heating 5 in alkali. 5-Carboxy-4-hydroxy-7-(/3-D-ribofuranosyl) pyirolo-[2, 3-c/jpyrimidine (8), synthesized from the intermediate 2-amino-4-carboxy-3-carbonyl-[lV-(2-carboxyethyl)]-l-/3-D-ribofuranosylpyrrole (7), bytreatment with formic acid and acetic anhydride was not radioactive. Compounds 2, 3, 4, 5, I-S uring the past 18 years 34 nucleoside antibiotics, having a wide spectrum of chemical structures and biological activity against viruses, bacterial, and tumor cells, have been isolated from the bacteria and fungi (Suhadolnik, 1970). The importance of adenine and/or adenosine in the biosynthesis of the nucleoside antibiotics, cordycepin (3'-deoxyadenosine), 3'-amino-3'-deoxyadenosine, 3'-acetamido-3'-deoxyadenosine, psicofuranine, decoyinine, tubercidin, and