3-Amino-4-hydroxybenzoic Acid Is Derived from the Tricarboxylic Acid Cycle Rather Than the Shikimic Acid Pathway

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• 作者：Steven J. Gould ; Chris R. Melville ; and Martha C. Cone
• 刊名：Journal of the American Chemical Society
• 出版年：1996
• 出版时间：October 2, 1996
• 年：1996
• 卷：118
• 期：39
• 页码：9228 - 9232
• 全文大小：341K
• 年卷期：v.118,no.39(October 2, 1996)
• ISSN：1520-5126

文摘

The biosynthesis of 4-hydroxy-3-nitrosobenzamide inStreptomyces murayamaensis mutants MC2andMC3 has been studied using sodium [1,2-¹³C₂]-and [1-¹³C,¹⁸O₂]acetate,sodium [2,3-¹³C₂]succinate,[1,2-¹³C₂]glutamicacid, [4-¹³C]aspartic acid, and sodium[1-¹³C]- and[2,3-¹³C₂]pyruvate. ¹³CNMR analysis of the labeling patternsfrom the first two of these suggested a pathway via condensation of afour-carbon unit from the tricarboxylic acid(TCA) cycle with a three-carbon unit, possibly phosphoenol pyruvate.Subsequent specific incorporations of thelabeled succinic acid, aspartic acid, and glutamic acid confirmed theTCA cycle involvement and the orientation ofthe four-carbon intermediate. Specific incorporation of thelabeled pyruvic acids confirmed the involvement of athree-carbon unit and defined its orientation. This is the firstaminohydroxybenzoic acid derivative shown not to bederived from a shikimic acid-type pathway, and its origin provides arationale for the biosynthesis of other microbialproducts such as asukamycin, manumycin, and themichigazones.