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阿维链霉菌合成阿维菌素。标记前体的掺入。

Biosynthesis of the avermectins by Streptomyces avermitilis. Incorporation of labeled precursors.

作者信息

Schulman M D, Valentino D, Hensens O

出版信息

J Antibiot (Tokyo). 1986 Apr;39(4):541-9. doi: 10.7164/antibiotics.39.541.

DOI:10.7164/antibiotics.39.541
PMID:3086265
Abstract

The biosynthesis of the avermectins, a group of 16 membered macrolides with potent anthelmintic and insecticidal activity produced by Streptomyces avermitilis, was studied by supplying cultures with 14C and 13C precursors. [1-14C] and [2-14C]acetate and propionate were poor precursors of the avermectins and were instead rapidly oxidized to 14CO2. The S-methyl of methionine in contrast was incorporated extensively and equally into the three methoxyl groups of the avermectins. The carbon backbone of methionine was not a precursor of the avermectins. Feeding of [1-13C]glucose yielded avermectins labeled specifically in the C1' and C1" of the oleandrose moiety and in the aglycone moiety in carbons known to be derived from the methyl of acetate. Feeding [U-13C]glucose showed that the entire avermectin molecule is derived from glucose carbons.

摘要

通过向阿维链霉菌培养物提供¹⁴C和¹³C前体,研究了阿维菌素(由阿维链霉菌产生的一组具有强大驱虫和杀虫活性的16元大环内酯类化合物)的生物合成。[1-¹⁴C]和[2-¹⁴C]乙酸盐和丙酸盐是阿维菌素的不良前体,反而会迅速氧化为¹⁴CO₂。相比之下,甲硫氨酸的S-甲基被广泛且等量地掺入到阿维菌素的三个甲氧基中。甲硫氨酸的碳骨架不是阿维菌素的前体。用[1-¹³C]葡萄糖喂养产生了在夹竹桃糖部分的C1'和C1"以及已知来自乙酸盐甲基的碳的苷元部分中特异性标记的阿维菌素。用[U-¹³C]葡萄糖喂养表明整个阿维菌素分子都来自葡萄糖碳。

相似文献

1
Biosynthesis of the avermectins by Streptomyces avermitilis. Incorporation of labeled precursors.阿维链霉菌合成阿维菌素。标记前体的掺入。
J Antibiot (Tokyo). 1986 Apr;39(4):541-9. doi: 10.7164/antibiotics.39.541.
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Studies on the biosynthesis of avermectins.阿维菌素生物合成的研究。
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Directed biosynthesis of avermectins.
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Branched-chain fatty acid requirement for avermectin production by a mutant of Streptomyces avermitilis lacking branched-chain 2-oxo acid dehydrogenase activity.阿维链霉菌缺乏支链2-氧代酸脱氢酶活性的突变体产生阿维菌素对支链脂肪酸的需求
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A second branched-chain alpha-keto acid dehydrogenase gene cluster (bkdFGH) from Streptomyces avermitilis: its relationship to avermectin biosynthesis and the construction of a bkdF mutant suitable for the production of novel antiparasitic avermectins.来自阿维链霉菌的第二个支链α-酮酸脱氢酶基因簇(bkdFGH):其与阿维菌素生物合成的关系以及构建适合生产新型抗寄生虫阿维菌素的bkdF突变体。
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"Streptomyces avermitilis" mutants defective in methylation of avermectins.阿维链霉菌中阿维菌素甲基化缺陷的突变体。
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Novel avermectins produced by mutational biosynthesis.通过突变生物合成产生的新型阿维菌素。
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Biosynthesis of the macrolide antibiotic chlorothricin: basic building blocks.大环内酯类抗生素氯丝菌素的生物合成:基本构建单元
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"Streptomyces avermitilis" mutants defective in methylation of avermectins.阿维链霉菌中阿维菌素甲基化缺陷的突变体。
Antimicrob Agents Chemother. 1987 May;31(5):744-7. doi: 10.1128/AAC.31.5.744.