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13C和15N标记的贝利那明及其降解产物的制备

Preparation of 13C and 15N labeled bellenamine and its degradation products.

作者信息

Ikeda Y, Naganawa H, Kondo S, Takeuchi T

机构信息

Institute of Microbial Chemistry, Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 1992 Dec;45(12):1925-9. doi: 10.7164/antibiotics.45.1925.

Abstract

A streptomyces metabolite, bellenamine, has been converted into D-beta-lysinamide and cyclized bellenamine in an acidic solution at 75 degrees C. The structure of the new cyclized compound was assigned as (R)-6-(3-aminopropyl)-1,3-diazacyclohexan-4-one by spectral analyses. [1-13C, Amide, 1'-15N2]bellenamine, which has been isolated from the culture by feeding both L-[1-13C]lysine and [15NH4]2SO4 to a synthetic medium, was degraded under acidic condition to obtain the stable isotope labeled D-beta-lysine, D-beta-lysinamide and cyclized bellenamine. These labeled compounds were analyzed by 13C and 15N NMR spectra, and will be used for the biosynthetic study on bellenamine.

摘要

一种链霉菌代谢产物——贝伦胺,在75℃的酸性溶液中已被转化为D-β-赖氨酸酰胺和环化贝伦胺。通过光谱分析,新环化化合物的结构被确定为(R)-6-(3-氨丙基)-1,3-二氮杂环己烷-4-酮。通过向合成培养基中同时添加L-[1-¹³C]赖氨酸和[¹⁵NH₄]₂SO₄从培养物中分离得到的[1-¹³C, 酰胺, 1'-¹⁵N₂]贝伦胺,在酸性条件下被降解以获得稳定同位素标记的D-β-赖氨酸、D-β-赖氨酸酰胺和环化贝伦胺。这些标记化合物通过¹³C和¹⁵N NMR光谱进行了分析,并将用于贝伦胺的生物合成研究。

相似文献

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Biosynthesis of bellenamine by Streptomyces nashvillensis using stable isotope labeled compounds.
J Antibiot (Tokyo). 1992 Dec;45(12):1919-24. doi: 10.7164/antibiotics.45.1919.
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Total syntheses of bellenamine and its isomers.贝伦胺及其异构体的全合成。
J Antibiot (Tokyo). 1992 Oct;45(10):1677-80. doi: 10.7164/antibiotics.45.1677.

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