3-AMINO-4-HYDROXYBENZOIC ACID IS DERIVED FROM THE TRICARBOXYLIC-ACID CYCLE RATHER THAN THE SHIKIMIC ACID PATHWAY

Citation
Sj. Gould et al., 3-AMINO-4-HYDROXYBENZOIC ACID IS DERIVED FROM THE TRICARBOXYLIC-ACID CYCLE RATHER THAN THE SHIKIMIC ACID PATHWAY, Journal of the American Chemical Society, 118(39), 1996, pp. 9228-9232
Citations number
29
Categorie Soggetti
Chemistry
ISSN journal
00027863
Volume
118
Issue
39
Year of publication
1996
Pages
9228 - 9232
Database
ISI
SICI code
0002-7863(1996)118:39<9228:3AIDFT>2.0.ZU;2-S
Abstract
The biosynthesis of 4-hydroxy-3-nitrosobenzamide in Streptomyces muray amaensis mutants MC2 and MC3 has been studied using sodium [1,2-C-13(2 )]- and [1-C-13,O-18(2)]acetate, sodium [2,3-C-13(2)]succinate, [1,2-C -13(2)]glutamic acid, [4-C-13]aspartic acid, and sodium [1-C-13]- and [2,3-C-13(2)]pyruvate. C-13 NMR analysis of the labeling patterns from the first two of these suggested a pathway via condensation of a four -carbon unit from the tricarboxylic acid (TCA) cycle with a three-carb on unit, possibly phosphoenol pyruvate. Subsequent specific incorporat ions of the labeled succinic acid, aspartic acid, and glutamic acid co nfirmed the TCA cycle involvement and the orientation of the four-carb on intermediate. Specific incorporation of the labeled pyruvic acids c onfirmed the involvement of a three-carbon unit and defined its orient ation. This is the first aminohydroxybenzoic acid derivative shown not to be derived from a shikimic acid-type pathway, and its origin provi des a rationale for the biosynthesis of other microbial products such as asukamycin, manumycin, and the michigazones.