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黄绿青霉中吡啶二羧酸的合成

Dipicolinic acid synthesis in Penicillium citreo-viride.

作者信息

Hodson P H, Foster J W

出版信息

J Bacteriol. 1966 Feb;91(2):562-9. doi: 10.1128/jb.91.2.562-569.1966.

DOI:10.1128/jb.91.2.562-569.1966
PMID:5883092
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC314895/
Abstract

Hodson, Phillip H. (University of Texas, Austin), and J. W. Foster. Dipicolinic acid synthesis in Penicillium citreo-viride. J. Bacteriol. 91:562-569. 1966.-Dipicolinic acid (DPA) accumulation in culture filtrates of the mold Penicillium citreo-viride was studied in surface and submerged cultures. Good DPA yields were obtained in suspensions of washed, submerged mycelium in the presence of a carbon and a nitrogen source but in the absence of other minerals essential for growth. Fumaric acid was the only other acid formed in significant amounts. Glucose and glycerol were superior to various salts of organic acids as carbon sources, and certain amino acids were excellent nitrogen sources. l-Leucine, l-norvaline, l-tyrosine, and l-histidine were superior to urea, NH(4)Cl, or NaNO(3) as nitrogen precursors for DPA production. d-Norvaline was useless for DPA production. Glycerol-2-C(14) and -1-C(14), C(14)O(2), and l-leucine-C(14), l-tyrosine-C(14), and l-histidine-C(14) were tested as precursors in conjunction with suitable carbon and nitrogen sources. The DPA was decarboxylated chemically, and the distribution of C(14) was determined in the pyridine-C and in the carboxyl-C. The data are consistent with Martin and Foster's suggestion for bacteria that the DPA molecule is formed by a condensation of C(3) plus C(4) precursors, the resulting 2-keto, 6-aminopimelic acid derivate undergoing ring closure to form a heterocyclic precursor of DPA. The C(14)O(2) experiments indicate that oxaloacetate is formed by beta-carboxylation of pyruvate, this in turn probably becoming aspartic acid beta-semialdehyde, the C(4) compound which condenses with a second pyruvate. The enhancement of DPA formation by l-norvaline, l-leucine, and l-histidine is not ascribable to their functioning either as a source of nitrogen or carbon. l-Tyrosine, in a glycerol medium, contributed nearly 40% of the DPA carbon. The mechanism of biosynthesis of C(7) straight-chain and cyclic compounds is discussed.

摘要

霍德森,菲利普·H.(得克萨斯大学奥斯汀分校)和J.W.福斯特。黄绿青霉中吡啶二羧酸的合成。《细菌学杂志》91:562 - 569。1966年。——研究了黄绿青霉霉菌培养滤液中吡啶二羧酸(DPA)在表面培养和深层培养中的积累情况。在有碳源和氮源但缺乏生长所需其他矿物质的条件下,洗涤后的深层菌丝体悬浮液中可获得较高的DPA产量。富马酸是大量形成的唯一其他酸。葡萄糖和甘油作为碳源优于各种有机酸盐,某些氨基酸是优良的氮源。L - 亮氨酸、L - 正缬氨酸、L - 酪氨酸和L - 组氨酸作为DPA生产的氮前体优于尿素、NH₄Cl或NaNO₃。D - 正缬氨酸对DPA生产无用。甘油 - 2 - C¹⁴和 - 1 - C¹⁴、¹⁴CO₂以及L - 亮氨酸 - C¹⁴、L - 酪氨酸 - C¹⁴和L - 组氨酸 - C¹⁴与合适的碳源和氮源一起作为前体进行了测试。DPA经化学脱羧,并测定了¹⁴C在吡啶 - C和羧基 - C中的分布。这些数据与马丁和福斯特对细菌的推测一致,即DPA分子由C₃加C₄前体缩合形成,生成的2 - 酮基、6 - 氨基庚二酸衍生物发生环化形成DPA的杂环前体。¹⁴CO₂实验表明草酰乙酸由丙酮酸的β - 羧化形成,这反过来可能变成天冬氨酸β - 半醛,即与第二个丙酮酸缩合反应的C₄化合物。L - 正缬氨酸、L - 亮氨酸和L - 组氨酸对DPA形成的促进作用并非归因于它们作为氮源或碳源的功能。在甘油培养基中,L - 酪氨酸贡献了近40%的DPA碳。讨论了C₇直链和环状化合物的生物合成机制。

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引用本文的文献

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本文引用的文献

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