A Three-Ring Circus: Metabolism of the Three Proteogenic Aromatic Amino Acids and Their Role in the Health of Plants and Animals

Abstract

Tyrosine, phenylalanine and tryptophan are the three aromatic amino acids (AAA) involved in protein synthesis. These amino acids and their metabolism are linked to the synthesis of a variety of secondary metabolites, a subset of which are involved in numerous anabolic pathways responsible for the synthesis of pigment compounds , plant hormones and biological polymers, to name a few. In addition, these metabolites derived from the AAA pathways mediate the transmission of nervous signals, quench reactive oxygen species in the brain, and are involved in the vast palette of animal coloration among others pathways. The AAA and metabolites derived from them also have integral roles in the health of both plants and animals. This review delineates the de novo biosynthesis of the AAA by microbes and plants, and the branching out of AAA metabolism into major secondary metabolic pathways in plants such as the phenylpropanoid pathway. Organisms that do not possess the enzymatic machinery for the de novo synthesis of AAA must obtain these primary metabolites from their diet. Therefore, the metabolism of AAA by the host animal and the resident microflora are important for the health of all animals. In addition, the AAA metabolite-mediated host-pathogen interactions in general, as well as potential beneficial and harmful AAA-derived compounds produced by gut bacteria are discussed. Apart from the AAA biosynthetic pathways in plants and microbes such as the shikimate pathway and the tryptophan pathway, this review also deals with AAA catabolism in plants, AAA degradation via the monoamine and kynurenine pathways in animals, and AAA catabolism via the 3-aryllactate and kynurenine pathways in animal-associated microbes. Emphasis will be placed on structural and functional aspects of several key AAA-related enzymes, such as shikimate synthase, chorismate mutase, anthranilate synthase, tryptophan synthase, tyrosine aminotransferase, dopachrome tautomerase, radical dehydratase, and type III CoA-transferase. The past development and current potential for interventions including the development of herbicides and antibiotics that target key enzymes in AAA-related pathways, as well as AAA-linked secondary metabolism leading to antimicrobials are also discussed.

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     Kane J. F. O'Brien H. D. (1975 ). p-Aminobenzoate synthase from Bacillus subtilis: amido-transferase composed of nonidentical subunits. J. Bacteriol. 123, 1131–1138.

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     Kaplan J. De Domenico I. Ward D. M. (2008 ). Chediak-Higashi syndrome. Current Opin. Hematol. 15, 22–29.

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     Kappock T. J. Caradonna J. B. (1996 ). Pterin-dependent amino acid hydroxylases. Chem. Rev. 96, 2659–2756.

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     Kawalleck P. Keller H. Hahlbrock K. Scheel D. Somssich I. E. (1993 ). A pathogen-responsive gene of parsley encodes tyrosine decarboxylase. J. Biol. Chem. 268, 2189–2194.

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     Keller U. Lang M. Crnovcic I. Pfennig F. Schauwecker F. (2010 ). The actinomycin biosynthetic gene cluster of Streptomyces chrysomallus: a genetic hall of mirrors for synthesis of a molecule with mirror symmetry. J. Bacteriol. 192, 2583–2595.

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     Kessler M. Terramani T. Lynch G. Baudry M. (1989 ). A glycine site associated with N-methyl-d-aspartic acid receptors: characterization and identification of a new class of antagonists. J. Neurochem. 52, 1319–1328.

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     Kim H. U. van Oostende C. Basset G. J. Browse J. (2008 ). The AAE14 gene encodes the Arabidopsis o-succinylbenzoyl-CoA ligase that is essential for phylloquinone synthesis and photosystem-I function. Plant J. 54, 272–283.

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     Kim J. Darley D. J. Buckel W. Pierik A. J. (2008 ). An allylic ketyl radical intermediate in clostridial amino-acid fermentation. Nature 452, 239–243.

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     Kim J. Hetzel M. Boiangiu C. D. Buckel W. (2004 ). Dehydration of (R)-2-hydroxyacyl-CoA to enoyl-CoA in the fermentation of α-amino acids by anaerobic bacteria. FEMS Microbiol. Rev. 28, 455–468.

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     Klipcan L. Moor N. Kessler N. Safro M. G. (2009 ). Eukaryotic cytosolic and mitochondrial phenylalanyl-tRNA synthetases catalyze the charging of tRNA with the meta-tyrosine. Proc. Natl Acad. Sci. U.S.A. 106, 11045–11048.

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     Knappskog P. M. Flatmark T. Mallet J. Lüdecke B. Bartholome K. (1994 ). Recessively inherited L-DOPA-responsive dystonia caused by a point mutation (Q381K) in the tyrosine hydroxylase gene. Hum. Mol. Genet. 4, 1209–1212.

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