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A Three-Ring Circus: Metabolism of the Three Proteogenic Aromatic Amino Acids and Their Role in the Health of Plants and Animals
Anutthaman Parthasarathy, Penelope J. Cross, Renwick C. J. Dobson and 3 more
Frontiers in Molecular Biosciences · 2018 · Review
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.
References 347
- 1.
Al Hafid N. Christodoulou J. (2015 ). Phenylketonuria: a review of current and future treatments. Transl. Pediatrics. 4, 304–317.
Not in our library10.3978/j.issn.2224-4336.2015.10.07
- 2.
Altendorf K. H. Gilch B. Lingens F. (1971 ). Biosynthesis of 4-aminobenzoic acid in Aerobacter aerogenes. FEBS Lett. 16, 95–98.
Not in our library10.1016/0014-5793(71)80341-1
- 3.
Alves-Ferreira M. Wellmer F. Banhara A. Kumar V. Riechmann J. L. Meyerowitz E. M. (2007 ). Global expression profiling applied to the analysis of Arabidopsis stamen development. Plant Physiol. 145, 747–762.
Not in our library10.1104/pp.107.104422
- 4.
Amireault P. Sibon D. Côté F. (2013 ). Life without peripheral serotonin: Insights from tryptophan hydroxylase 1 knockout mice reveal the existence of paracrine/autocrine serotonergic networks. ACS Chem. Neurosci. 4, 64–71.
Not in our library10.1021/cn300154j
- 5.
Anterola A. M. Lewis N. G. (2002 ). Trends in lignin modification: a comprehensive analysis of the effects of genetic manipulations/mutations on lignification and vascular integrit. Phytochemistry 61, 221–294.
Not in our library10.1016/s0031-9422(02)00211-x
- 6.
Arnao M. B. Hernández-Ruiz J. (2015 ). Functions of melatonin in plants: a review. J. Pineal Res. 59, 133–150.
Not in our library10.1111/jpi.12253
- 7.
Aroca P. Garcia-Borron J. C. Solano F. Lozano J. A. (1990b ). Regulation of mammalian melanogenesis I: partial purification and characterization of a dopachrome converting factor: Dopachrome tautomerase. Biochim. Biophys. Acta. 1035, 266–275.
Not in our library10.1016/0304-4165(90)90088-e
- 8.
Aroca P. Solano F. García-Borrón J. C. Lozano J. A. (1990a ). A new spectrophotometric assay for dopachrome tautomerase. J. Biochem. Biophys. Methods. 21, 35–46.
Not in our library10.1016/0165-022x(90)90043-c
- 9.
Ashenafi M. Reddy P. T. Parsons J. F. Byrnes W. M. (2015 ). The fused anthranilate synthase from Streptomyces venezuelae functions as a monomer. Mol. Cell. Biochem. 400, 9–15.
Not in our library10.1007/s11010-014-2256-3
- 10.
Aso Y. Imamura Y. Yamasaki N. (1989 ). Further studies on dopa quinone imine conversion factor from the cuticles of Manduca sexta (L.). Insect Biochem. 19, 401–407.
Not in our library10.1016/0020-1790(89)90045-0
- 11.
Aso Y. Kramer K. J. Hopkins T. L. Whetzel S. Z. (1984 ). Properties of tyrosinase and dopa quinone imine conversion factor from pharate pupal cuticle of Manduca sexta. Insect Biochem. 14, 463–472.
Not in our library10.1016/0020-1790(84)90103-3
- 12.
Axe J. M. Boehr D. D. (2013 ). Long-range interactions in the α subunit of tryptophan synthase help to coordinate ligand binding, catalysis, and substrate channeling. J. Mol. Biol. 425, 1527–1545.
Not in our library10.1016/j.jmb.2013.01.030
- 13.
Bader J. Simon H. (1983 ). ATP formation is coupled to the hydrogenation of 2-enoates in Clostridium sporogenes. FEMS Microbiol. Lett. 20, 171–175.
Not in our library10.1111/j.1574-6968.1983.tb00111.x
- 14.
Baldwin E. Goodner K. Plotto A. Pritchett K. Einstein M. (2004 ). Effect of volatiles and their concentration on perception of tomato descriptors. J. Food Sci. 69, 310–318.
Not in our library10.1111/j.1750-3841.2004.tb18023.x
- 15.
Barker J. L. Frost J. W. (2001 ). Microbial synthesis of p-hydroxybenzoic acid from glucose. Biotechnol. Bioeng. 76, 376–390.
Not in our library10.1002/bit.10160
- 16.
Bartel B. LeClere S. Magidin M. Zolman B. K. (2001 ). Inputs to the active indole-3-acetic acid pool: de novo synthesis, conjugate hydrolysis, and indole-3-butyric acid b-oxidation. J. Plant Growth Regul. 20, 198–216.
Not in our library10.1007/s003440010025
- 17.
Bashiri G. Johnston J. M. Evans G. L. Bulloch E. M. Goldstone D. C. Jirgis E. N.. (2015 ). Structure and inhibition of subunit I of the anthranilate synthase complex of Mycobacterium tuberculosis and expression of the active complex. Acta Crystallogr. D Biol. Crystallogr. 71, 2297–2308
Not in our library10.1107/s1399004715017216
- 18.
Basset G. J. Quinlivan E. P. Ravanel S. Rébeill,é F. Nichols B. P. Shinozaki K.. (2004 ). Folate synthesis in plants: the p-aminobenzoate branch is initiated by a bifunctional PabA–PabB protein that is targeted to plastids. Proc. Natl Acad. Sci. U S A. 101, 1496–1501.
Not in our library10.1073/pnas.0308331100
- 19.
Ben Zvi M. M. Negre-Zakharov F. Masci T. Ovadis M. Shklarman E. Ben-Meir H.. (2008 ). Interlinking showy traits: co-engineering of scent and colour biosynthesis in flowers. Plant Biotechnol. J. 6, 403–415.
Not in our library10.1111/j.1467-7652.2008.00329.x
- 20.
Bender D. A. (2012 ). The Aromatic Amino Acids: Phenylalanine, Tyrosine, and Tryptophan. Amino Acid Metabolism, 3rd Edn. Chichester: Wiley.
Not in our library
- 21.
Bendheim P. E. Poeggeler B. Neria E. Ziv V. Pappolla M. A. Chain D. G. (2002 ). Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease. J. Mol. Neurosci. 19, 213-217.
Not in our library10.1007/s12031-002-0036-0
- 22.
Bendrat K. Müller U. Klees A. G. Buckel W. (1993 ). Identification of the gene encoding the activator of (R)-2-hydroxyglutaryl-CoA dehydratase from Acidaminococcus fermentans by gene expression in Escherichia coli. FEBS J. 329, 329–331.
Not in our library10.1016/0014-5793(93)80247-r
- 23.
Benesova M. Bode R. (1992 ). Chorismate mutase isoforms from seeds and seedlings of Papaver somniferum. Phytochemistry, 31, 2983–2987.
Not in our library10.1016/0031-9422(92)83431-w
- 24.
Benkov,á E. Michniewicz M. Sauer M. (2003 ). Local, efflux-dependent auxin gradients as a common module for plant organ formation. Cell 115, 591–602.
Not in our library10.1016/s0092-8674(03)00924-3
- 25.
Berger M. Gray J. A. Roth B. L. (2009 ). The expanded biology of serotonin. Annu. Rev. Med. 60, 355–366.
Not in our library10.1146/annurev.med.60.042307.110802
- 26.
Berk H. Buckel W. Thauer R. K. Frey P. A. (1996 ). Re-face stereospecificity at C4 of NAD(P) for alcohol dehydrogenase from Methanogenium organophilum and for (R)-2-hydroxyglutarate dehydrogenase fromAcidaminococcus fermentans as determined by 1H-NMR spectroscopy. FEBS Lett. 399, 92–94.
Not in our library10.1016/s0014-5793(96)01292-6
- 27.
Bertin C. Weston L. A. Huang T. Jander G. Owens T. Meinwald J.. (2007 ). Grass roots chemistry: meta-tyrosine, an herbicidal nonprotein amino acid. Proc. Natl. Acad. Sci. U.S.A. 104, 16964–16969.
Not in our library10.1073/pnas.0707198104
- 28.
Bickel H. Plame L. Schultz G. (1978 ). Incorporation of shikimate and other precursors into aromatic amino acids and preylquinones of isolated spinach chloroplasts. Phytochemistry 17, 119–124.
Not in our library10.1016/s0031-9422(00)89691-0
- 29.
Blackmore N. J. Reichau S. Jaio W. Hutton R. D. Baker E. N. Jameson G. B.. (2013 ). Three sites and you are out: ternary synergistic allostery controls aromatic amino acid biosynthesis in Mycobacterium tuberculosis. J. Mol. Biol. 425, 1582–1592.
Not in our library10.1016/j.jmb.2012.12.019
- 30.
Blanco B. Prado V. Lence E. Otero J. M. García-Doval C. van Raaij M. J.. (2013 ). Mycobacterium tuberculosis shikimate kinase inhibitors: design and simulation studies of the catalytic turnover. J. Am. Chem. Soc. 135, 12366–12376.
Not in our library10.1021/ja405853p
- 31.
Blomberg L. M. Mangold M. Mitchell J. B. Blumberger J. (2009 ). Theoretical study of the reaction mechanism of Streptomyces coelicolor type II dehydroquinase. J. Chem. Theory Comput. 5, 1284–1294.
Not in our library10.1021/ct800480d
- 32.
Böttcher C. Westphal L. Schmotz C. Prade E. Scheel D. Glawischnig E. (2009 ). The multifunctional enzyme CYP71B15 (PHYTOALEXIN DEFICIENT3) converts cysteine-indole-3-acetonitrile to camalexin in the indole-3-acetonitrile metabolic network of Arabidopsis thaliana. Plant Cell. 21, 1830–1845.
Not in our library10.1105/tpc.109.066670
- 33.
Boudet A. (2007 ). Evolution and current status of phenolic compounds. Phytochemistry. 68, 2722–2735.
Not in our library10.1016/j.phytochem.2007.06.012
- 34.
Brannon D. R. Mabe J. A. Molloy B. B. Day W. A. (1971 ). Biosynthesis of dithiadiketopiperazine antibiotics: comparison of possible aromatic amino acid precursors. Biochem. Biophys. Res. Comm. 43, 588–594.
Not in our library10.1016/0006-291x(71)90654-1
- 35.
Broadley K. J. (2010 ). The vascular effects of trace amines and amphetamines. Pharmacol. Ther. 125, 363–375.
Not in our library10.1016/j.pharmthera.2009.11.005
- 36.
Brown D. R. Kenyon G. L. Hegeman G. D. (1970 ). Incorporation of monofluorotryptophans into protein during the growth of Escherichia coli. Biochem. Biophys. Res. Comm. 39, 13–19.
Not in our library10.1016/0006-291x(70)90750-3
- 37.
Brunke S. Seider K. Richter M. E. Bremer-Streck S. Ramachandra S. Kiehntopf M.. (2014 ). Histidine degradation via an aminotransferase increases the nutritional flexibility of Candida glabrata. Eukaryot. Cell 13, 758–765.
Not in our library10.1128/ec.00072-14
- 38.
Buchanan B. Gruissem W. Jones R. L. (eds) (2000 ). Biochemistry and Molecular Biology of Plants. Rockville, MD: American Society of Plant Biologists.
Not in our library
- 39.
Buckel W. (2001 ). Unusual enzymes involved in five pathways of glutamate fermentation. Appl. Microbiol. Biotechnol. 57, 263–273.
Not in our library10.1007/s002530100773
- 40.
Buckel W. Keese R. (1995 ). One-electron redox reactions of CoASH esters in anaerobic bacteria - a mechanistic proposal. Angew. Chem. Internat. Ed. Eng. 34, 1502–1506.
Not in our library10.1002/anie.199515021
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