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安莎霉素生物合成:对从地中海诺卡氏菌突变株中分离出的一种新型利福霉素的研究。

Ansamycin biogenesis: studies on a novel rifamycin isolated from a mutant strain of Nocardia mediterranei.

作者信息

White R J, Martinelli E, Lancini G

出版信息

Proc Natl Acad Sci U S A. 1974 Aug;71(8):3260-4. doi: 10.1073/pnas.71.8.3260.

Abstract

A novel ansamycin, rifamycin W, was isolated from a mutant strain of Nocardia mediterranei. The metabolic origin of rifamycin W was studied by (13)C nuclear magnetic resonance spectroscopy. Examination of the proton-decoupled pulse and Fourier transform (13)C spectra of rifamycin W biogenetically enriched with [1-(13)C]-, [2-(13)C]-, and [3-(13)C]propionate and with [1-(13)C]acetate has revealed that the alignment of acetate and propionate units corresponds to that previously proposed for rifamycin S. Washed mycelium from a rifamycin B-producing strain of N. mediterranei transformed rifamycin W into rifamycin B. We suggest that rifamycin W is a normal intermediate in the biosynthesis of the other rifamycins. These results, together with the structural similarity of rifamycin W to the streptovaricins, reinforce our hypothesis that a common progenitor is involved in the biogenesis of all naphthalenic ansamycins.

摘要

从地中海诺卡氏菌的一个突变株中分离出一种新型安莎霉素——利福霉素W。通过碳-13核磁共振光谱研究了利福霉素W的代谢起源。对用[1-(13)C]-、[2-(13)C]-和[3-(13)C]丙酸酯以及[1-(13)C]乙酸酯进行生物合成富集的利福霉素W的质子去耦脉冲和傅里叶变换碳-13光谱的研究表明,乙酸酯和丙酸酯单元的排列与先前对利福霉素S所提出的排列一致。来自地中海诺卡氏菌的一个产利福霉素B菌株的洗涤菌丝体将利福霉素W转化为利福霉素B。我们认为利福霉素W是其他利福霉素生物合成中的正常中间体。这些结果,连同利福霉素W与链黑菌素的结构相似性,强化了我们的假设,即所有萘并安莎霉素的生物合成都涉及一个共同的前体。

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本文引用的文献

1
Streptovaricin. I. Discovery and biologic activity.链黑菌素。一、发现及生物活性。
Am Rev Tuberc. 1957 Apr;75(4):576-83. doi: 10.1164/artpd.1957.75.4.576.
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Geldanamycin, a new antibiotic.格尔德霉素,一种新型抗生素。
J Antibiot (Tokyo). 1970 Sep;23(9):442-7. doi: 10.7164/antibiotics.23.442.
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[The biogenesis of rifamycin S].[利福霉素S的生物合成]
Helv Chim Acta. 1973 Jul;56(7):2315-23. doi: 10.1002/hlca.19730560718.

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