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首页> 外文期刊>The Journal of Antibiotics: An International Journal >Investigation of the biosynthesis of the pipecolate moiety of neuroprotective polyketide meridamycin.
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Investigation of the biosynthesis of the pipecolate moiety of neuroprotective polyketide meridamycin.

机译：神经保护性聚酮化合物美利达霉素的哌酸酯部分的生物合成研究。

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Biogenesis of the pipecolate moiety of neuroprotective agent meridamycin in Streptomyces sp. NRRL30748 was investigated in feeding studies using lysine specifically labeled with (15)N at the alpha-amino or the epsilon-amino nitrogen position. Fourier transform mass spectrometry analysis with ultra-high mass resolving power and accurate mass measurement capability was employed to resolve the (15)N peak of labeled meridamycin from the (13)C peak of unlabeled meridamycin, allowing the precise calculation of labeling contents under each condition. The relative enrichment of (15)N-labeled meridamycin was ~43% with L-[alpha-(15)N]-lysine feeding and ~14% with L-[alpha-(15)N]-lysine feeding, suggesting two distinguishable pathways, with concomitant loss of either the epsilon-amino group or the alpha-amino group of lysine, were involved in the generation of the pipecolate moiety of meridamycin in this bacterium. PCR cloning using degenerate primers identified a proC gene encoding a putative pyrroline-5-carboxylate reductase, which was expected to catalyze the conversion of piperideine-6-carboxylate to pipecolate. However, inactivation of this locus did not significantly affect the incorporation of alpha-(15)N- or epsilon-(15)N-labeled lysine into meridamycin, indicating the existence of an alternative route for the last step of the lysine epsilon-transamination pathway. This work revealed the diversity and complexity of the biosynthetic pathways for pipecolate synthesis in the meridamycin producing bacterium Streptomyces sp. NRRL30748.
机译：链霉菌属中神经保护剂美利达霉素的pipecolate部分的生物发生。 NRRL30748在饲喂研究中使用在α-氨基或ε-氨基氮位置上特别标记有（15）N的赖氨酸进行了研究。使用具有超高质量分辨能力和精确质量测量功能的傅里叶变换质谱分析法，从未标记的美达霉素的（13）C峰中分辨出标记的美达霉素的（15）N峰，从而可以精确计算每种条件下的标记含量健康）状况。饲喂L-α-（15）N]-赖氨酸时（15）N标记的美达霉素的相对富集度为〜43％，饲喂L-α-（15）N]-赖氨酸时的相对富集度为〜14％，表明两个可区分的途径，伴随着赖氨酸的ε-氨基或赖氨酸的α-氨基的丢失，都参与了该细菌美利达霉素的pipecolate部分的产生。使用简并引物进行PCR克隆，鉴定出编码推定的吡咯啉-5-羧酸盐还原酶的proC基因，该基因有望催化哌啶-6-羧酸盐转化为哌啶盐。然而，该基因座的灭活并没有显着影响将α-（15）N-或ε-（15）N标记的赖氨酸掺入美立霉素，表明赖氨酸ε-转氨作用的最后一步存在替代途径途径。这项工作揭示了产美达霉素的链霉菌属细菌Streptomyces sp。中胡椒酸酯合成的生物合成途径的多样性和复杂性。 NRRL30748。

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