Phenylpyruvate (BioDeep_00000001693)

 

Secondary id: BioDeep_00000405215, BioDeep_00000870067

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


Metabolite Card


2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)

Formula: C9H8O3 (164.0473418)
Chinese Names: 苯丙酮酸, 苯丙酮酸钠
Spectrum Hits: Top Source Homo sapiens(blood) 0.14%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Phenylpyruvate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/phenylpyruvate (retrieved 2024-11-07) (BioDeep RN: BioDeep_00000001693). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Molecular Structure

SMILES: C1=CC=C(C=C1)CC(=O)C(=O)O
InChI: InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

Description

Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. Phenylpyruvic acid is also a microbial metabolite, it can be produced by Lactobacillus plantarum (PMID: 9687465).
Flavouring ingredient
Phenylpyruvic acid is used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase[1].
Phenylpyruvic acid is used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase[1].

Synonyms

46 synonym names

2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto); alpha-Oxo-benzenepropanoic acid; alpha-Oxobenzenepropionic acid; α-Ketohydrocinnamic acid; alpha-Oxobenzenepropanoic acid; 2-Oxo-3-phenylpropanoic acid; 3-Phenyl-2-oxopropionic acid; alpha-Ketohydrocinnamic acid; 3-Phenyl-2-oxopropanoic acid; 2-Oxo-3-phenylpropionic acid; alpha-Oxo-benzenepropanoate; a-Oxo-benzenepropanoic acid; α-Oxo-benzenepropanoic acid; α-Ketohydrocinnamate; α-Oxobenzenepropionic acid; α-Oxobenzenepropanoic acid; β-Phenylpyruvic acid; Phenylbrenztraubensaeure; 3-Phenyl-2-oxopropanoate; 2-Oxo-3-phenylpropanoate; alpha-Ketohydrocinnamate; α-Ketohydrocinnamic acid; a-Ketohydrocinnamic acid; a-Oxo-benzenepropanoate; beta-Phenylpyruvic acid; keto-Phenylpyruvic acid; α-Oxo-benzenepropanoate; a-Hydroxycinnamic acid; Phenylpyroracemic acid; β-Phenylpyruvate; Sodium phenylpyruvate; a-Ketohydrocinnamate; α-Ketohydrocinnamate; b-Phenylpyruvic acid; β-Phenylpyruvic acid; 3-Phenylpyruvic acid; beta-Phenylpyruvate; Keto-phenylpyruvate; Phenylpyroracemate; Phenylpyruvic acid; b-Phenylpyruvate; 3-PHENYLPYRUVate; β-Phenylpyruvate; Phenylpyruvate; FEMA 3892; Phenylpyruvic acid



Cross Reference

27 cross reference id

Classification Terms

Related Pathways

Reactome(0)

BioCyc(1)

PlantCyc(0)

Biological Process

513 related biological process reactions.

Reactome(0)

BioCyc(6)

WikiPathways(0)

Plant Reactome(484)

INOH(3)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(20)

PharmGKB(0)

6 organism taxonomy source information

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



Literature Reference

  • Anne Jahn, Maike Petersen. Hydroxy(phenyl)pyruvic acid reductase in Actaea racemosa L.: a putative enzyme in cimicifugic and fukinolic acid biosynthesis. Planta. 2024 Mar; 259(5):102. doi: 10.1007/s00425-024-04382-6. [PMID: 38549005]
  • Zuanxian Su, Qiushen Xiao, Jiyuan Shen, Houbin Chen, Shijuan Yan, Wenjie Huang. Metabolomics Analysis of Litchi Leaves during Floral Induction Reveals Metabolic Improvement by Stem Girdling. Molecules (Basel, Switzerland). 2021 Jul; 26(13):. doi: 10.3390/molecules26134048. [PMID: 34279388]
  • Anne Daly, Sharon Evans, Alex Pinto, Catherine Ashmore, Anita MacDonald. Protein Substitutes in PKU; Their Historical Evolution. Nutrients. 2021 Feb; 13(2):. doi: 10.3390/nu13020484. [PMID: 33540516]
  • Kyeongwoo Jang, W Seth Horne, Sanford A Asher. Human Serum Phenylpyruvate Quantification Using Responsive 2D Photonic Crystal Hydrogels via Chemoselective Oxime Ligation: Progress toward Developing Phenylalanine-Sensing Elements. ACS applied materials & interfaces. 2020 Sep; 12(35):39612-39619. doi: 10.1021/acsami.0c08787. [PMID: 32805910]
  • Joseph H Lynch, Yichun Qian, Longyun Guo, Itay Maoz, Xing-Qi Huang, Alekzander S Garcia, Gordon Louie, Marianne E Bowman, Joseph P Noel, John A Morgan, Natalia Dudareva. Modulation of auxin formation by the cytosolic phenylalanine biosynthetic pathway. Nature chemical biology. 2020 08; 16(8):850-856. doi: 10.1038/s41589-020-0519-8. [PMID: 32284603]
  • Amsha Viraragavan, Nokulunga Hlengwa, Dalene de Beer, Sylvia Riedel, Neil Miller, Sandra Bowles, Beata Walczak, Christo Muller, Elizabeth Joubert. Model development for predicting in vitro bio-capacity of green rooibos extract based on composition for application as screening tool in quality control. Food & function. 2020 Apr; 11(4):3084-3094. doi: 10.1039/c9fo02480h. [PMID: 32195502]
  • Yichun Qian, Joseph H Lynch, Longyun Guo, David Rhodes, John A Morgan, Natalia Dudareva. Completion of the cytosolic post-chorismate phenylalanine biosynthetic pathway in plants. Nature communications. 2019 01; 10(1):15. doi: 10.1038/s41467-018-07969-2. [PMID: 30604768]
  • Fei Qiu, Chunxian Yang, Lina Yuan, Dan Xiang, Xiaozhong Lan, Min Chen, Zhihua Liao. A Phenylpyruvic Acid Reductase Is Required for Biosynthesis of Tropane Alkaloids. Organic letters. 2018 12; 20(24):7807-7810. doi: 10.1021/acs.orglett.8b03236. [PMID: 30511859]
  • Mei Ru, Kunru Wang, Zhenqing Bai, Liang Peng, Shaoxuan He, Yong Wang, Zongsuo Liang. A tyrosine aminotransferase involved in rosmarinic acid biosynthesis in Prunella vulgaris L. Scientific reports. 2017 07; 7(1):4892. doi: 10.1038/s41598-017-05290-4. [PMID: 28687763]
  • Natalia I Agalakova, Irina V Brailovskaya, Svetlana A Konovalova, Sergei M Korotkov, Elena A Lavrova, Anatolii A Nikiforov. ATP-consuming processes in hepatocytes of river lamprey Lampetra fluviatilis on the course of prespawning starvation. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2016 11; 201(?):95-100. doi: 10.1016/j.cbpa.2016.07.002. [PMID: 27399971]
  • Jorge El-Azaz, Fernando de la Torre, Concepción Ávila, Francisco M Cánovas. Identification of a small protein domain present in all plant lineages that confers high prephenate dehydratase activity. The Plant journal : for cell and molecular biology. 2016 07; 87(2):215-29. doi: 10.1111/tpj.13195. [PMID: 27125254]
  • Huawei Zhang, Peng Fu, Beilei Ke, Shuping Wang, Min Li, Lin Han, Chengcheng Peng, Weidong Zhang, Runhui Liu. Metabolomic analysis of biochemical changes in the plasma and urine of collagen-induced arthritis in rats after treatment with Huang-Lian-Jie-Du-Tang. Journal of ethnopharmacology. 2014 May; 154(1):55-64. doi: 10.1016/j.jep.2014.03.007. [PMID: 24709313]
  • Till Pfennig, Beate Herrmann, Tim Bauer, Edgar Schömig, Dirk Gründemann. Benzoic acid and specific 2-oxo acids activate hepatic efflux of glutamate at OAT2. Biochimica et biophysica acta. 2013 Feb; 1828(2):491-8. doi: 10.1016/j.bbamem.2012.08.026. [PMID: 22981274]
  • Heejin Yoo, Joshua R Widhalm, Yichun Qian, Hiroshi Maeda, Bruce R Cooper, Amber S Jannasch, Itay Gonda, Efraim Lewinsohn, David Rhodes, Natalia Dudareva. An alternative pathway contributes to phenylalanine biosynthesis in plants via a cytosolic tyrosine:phenylpyruvate aminotransferase. Nature communications. 2013; 4(?):2833. doi: 10.1038/ncomms3833. [PMID: 24270997]
  • Ziyin Yang, Eiji Kobayashi, Tsuyoshi Katsuno, Toshimichi Asanuma, Tamaki Fujimori, Takamasa Ishikawa, Miho Tomomura, Kazuo Mochizuki, Takaya Watase, Yoriyuki Nakamura, Naoharu Watanabe. Characterisation of volatile and non-volatile metabolites in etiolated leaves of tea (Camellia sinensis) plants in the dark. Food chemistry. 2012 Dec; 135(4):2268-76. doi: 10.1016/j.foodchem.2012.07.066. [PMID: 22980801]
  • Dylan K Kosma, Isabel Molina, John B Ohlrogge, Mike Pollard. Identification of an Arabidopsis fatty alcohol:caffeoyl-Coenzyme A acyltransferase required for the synthesis of alkyl hydroxycinnamates in root waxes. Plant physiology. 2012 Sep; 160(1):237-48. doi: 10.1104/pp.112.201822. [PMID: 22797656]
  • T Andrew Clayton. Metabolic differences underlying two distinct rat urinary phenotypes, a suggested role for gut microbial metabolism of phenylalanine and a possible connection to autism. FEBS letters. 2012 Apr; 586(7):956-61. doi: 10.1016/j.febslet.2012.01.049. [PMID: 22306194]
  • Yuki Tobimatsu, Sasikumar Elumalai, John H Grabber, Christy L Davidson, Xuejun Pan, John Ralph. Hydroxycinnamate conjugates as potential monolignol replacements: in vitro lignification and cell wall studies with rosmarinic acid. ChemSusChem. 2012 Apr; 5(4):676-86. doi: 10.1002/cssc.201100573. [PMID: 22359379]
  • Simplice D Karou, Tchadjobo Tchacondo, Micheline Agassounon Djikpo Tchibozo, Kokou Anani, Lassina Ouattara, Jacques Simpore, Comlan de Souza. Screening Togolese medicinal plants for few pharmacological properties. Pharmacognosy research. 2012 Apr; 4(2):116-22. doi: 10.4103/0974-8490.94737. [PMID: 22518084]
  • Hiroshi Hirata, Toshiyuki Ohnishi, Haruka Ishida, Kensuke Tomida, Miwa Sakai, Masakazu Hara, Naoharu Watanabe. Functional characterization of aromatic amino acid aminotransferase involved in 2-phenylethanol biosynthesis in isolated rose petal protoplasts. Journal of plant physiology. 2012 Mar; 169(5):444-51. doi: 10.1016/j.jplph.2011.12.005. [PMID: 22236980]
  • Janak Kishore. Isolation, identification & characterization of Proteus penneri--a missed rare pathogen. The Indian journal of medical research. 2012 Mar; 135(?):341-5. doi: . [PMID: 22561620]
  • Angelique Stalmach, Christine A Edwards, Jolynne D Wightman, Alan Crozier. Gastrointestinal stability and bioavailability of (poly)phenolic compounds following ingestion of Concord grape juice by humans. Molecular nutrition & food research. 2012 Mar; 56(3):497-509. doi: 10.1002/mnfr.201100566. [PMID: 22331633]
  • F Khater, D Fournand, S Vialet, E Meudec, V Cheynier, N Terrier. Identification and functional characterization of cDNAs coding for hydroxybenzoate/hydroxycinnamate glucosyltransferases co-expressed with genes related to proanthocyanidin biosynthesis. Journal of experimental botany. 2012 Feb; 63(3):1201-14. doi: 10.1093/jxb/err340. [PMID: 22090445]
  • Jian Liu, Jun Zhou, Da Xing. Phosphatidylinositol 3-kinase plays a vital role in regulation of rice seed vigor via altering NADPH oxidase activity. PloS one. 2012; 7(3):e33817. doi: 10.1371/journal.pone.0033817. [PMID: 22448275]
  • Christin Fellenberg, Jörg Ziegler, Vinzenz Handrick, Thomas Vogt. Polyamine Homeostasis in Wild Type and Phenolamide Deficient Arabidopsis thaliana Stamens. Frontiers in plant science. 2012; 3(?):180. doi: 10.3389/fpls.2012.00180. [PMID: 22912643]
  • Arjun Sengupta, Soumita Ghosh, Angika Basant, Suhas Malusare, Parul Johri, Sulabha Pathak, Shobhona Sharma, Haripalsingh M Sonawat. Global host metabolic response to Plasmodium vivax infection: a 1H NMR based urinary metabonomic study. Malaria journal. 2011 Dec; 10(?):384. doi: 10.1186/1475-2875-10-384. [PMID: 22196439]
  • Rogelio Santiago, Ana Butrón, Pedro Revilla, Rosa Ana Malvar. Is the basal area of maize internodes involved in borer resistance?. BMC plant biology. 2011 Oct; 11(?):137. doi: 10.1186/1471-2229-11-137. [PMID: 21999882]
  • Hande Karaköse, Rakesh Jaiswal, Nikolai Kuhnert. Characterization and quantification of hydroxycinnamate derivatives in Stevia rebaudiana leaves by LC-MSn. Journal of agricultural and food chemistry. 2011 Sep; 59(18):10143-50. doi: 10.1021/jf202185m. [PMID: 21806067]
  • Zhoutong Sun, Yuanyuan Ning, Lixia Liu, Yingmiao Liu, Bingbing Sun, Weihong Jiang, Chen Yang, Sheng Yang. Metabolic engineering of the L-phenylalanine pathway in Escherichia coli for the production of S- or R-mandelic acid. Microbial cell factories. 2011 Sep; 10(?):71. doi: 10.1186/1475-2859-10-71. [PMID: 21910908]
  • Amanda J Lloyd, J William Allwood, Catherine L Winder, Warwick B Dunn, James K Heald, Simona M Cristescu, Anushen Sivakumaran, Frans J M Harren, Joseph Mulema, Katherine Denby, Royston Goodacre, Aileen R Smith, Luis A J Mur. Metabolomic approaches reveal that cell wall modifications play a major role in ethylene-mediated resistance against Botrytis cinerea. The Plant journal : for cell and molecular biology. 2011 Sep; 67(5):852-68. doi: 10.1111/j.1365-313x.2011.04639.x. [PMID: 21575089]
  • Crystal D Bross, Oliver R A Corea, Angelo Kaldis, Rima Menassa, Mark A Bernards, Susanne E Kohalmi. Complementation of the pha2 yeast mutant suggests functional differences for arogenate dehydratases from Arabidopsis thaliana. Plant physiology and biochemistry : PPB. 2011 Aug; 49(8):882-90. doi: 10.1016/j.plaphy.2011.02.010. [PMID: 21388819]
  • Valeriano Dal Cin, Denise M Tieman, Takayuki Tohge, Ryan McQuinn, Ric C H de Vos, Sonia Osorio, Eric A Schmelz, Mark G Taylor, Miriam T Smits-Kroon, Robert C Schuurink, Michel A Haring, James Giovannoni, Alisdair R Fernie, Harry J Klee. Identification of genes in the phenylalanine metabolic pathway by ectopic expression of a MYB transcription factor in tomato fruit. The Plant cell. 2011 Jul; 23(7):2738-53. doi: 10.1105/tpc.111.086975. [PMID: 21750236]
  • Valentina L Kouznetsova, Igor F Tsigelny, Megha A Nagle, Sanjay K Nigam. Elucidation of common pharmacophores from analysis of targeted metabolites transported by the multispecific drug transporter-Organic anion transporter1 (Oat1). Bioorganic & medicinal chemistry. 2011 Jun; 19(11):3320-40. doi: 10.1016/j.bmc.2011.04.045. [PMID: 21571536]
  • Dongli Zhang, Wenli Li, Junbo Zhang, Wanrong Tang, Chenxu Qian, Minghao Feng, Qingcui Chu, Jiannong Ye. Study on urinary metabolic profile of phenylketonuria by micellar electrokinetic capillary chromatography with dual electrochemical detection--potential clinical application in fast diagnosis of phenylketonuria. Analytica chimica acta. 2011 May; 694(1-2):61-6. doi: 10.1016/j.aca.2011.03.044. [PMID: 21565303]
  • Lindsey K Tuominen, Virgil E Johnson, Chung-Jui Tsai. Differential phylogenetic expansions in BAHD acyltransferases across five angiosperm taxa and evidence of divergent expression among Populus paralogues. BMC genomics. 2011 May; 12(?):236. doi: 10.1186/1471-2164-12-236. [PMID: 21569431]
  • Jia V Li, Jasmina Saric, Yulan Wang, Jürg Utzinger, Elaine Holmes, Oliver Balmer. Metabonomic investigation of single and multiple strain Trypanosoma brucei brucei infections. The American journal of tropical medicine and hygiene. 2011 Jan; 84(1):91-8. doi: 10.4269/ajtmh.2011.10-0402. [PMID: 21212208]
  • Chimezie Jason Ogugbue, Thomas Sawidis. Bioremediation and Detoxification of Synthetic Wastewater Containing Triarylmethane Dyes by Aeromonas hydrophila Isolated from Industrial Effluent. Biotechnology research international. 2011; 2011(?):967925. doi: 10.4061/2011/967925. [PMID: 21808740]
  • Vered Tzin, Gad Galili. New insights into the shikimate and aromatic amino acids biosynthesis pathways in plants. Molecular plant. 2010 Nov; 3(6):956-72. doi: 10.1093/mp/ssq048. [PMID: 20817774]
  • Diane Dobberstein, Mirko Bunzel. Identification of ferulate oligomers from corn stover. Journal of the science of food and agriculture. 2010 Aug; 90(11):1802-10. doi: 10.1002/jsfa.4017. [PMID: 20549649]
  • David R Holding, Robert B Meeley, Jan Hazebroek, David Selinger, Fred Gruis, Rudolf Jung, Brian A Larkins. Identification and characterization of the maize arogenate dehydrogenase gene family. Journal of experimental botany. 2010 Aug; 61(13):3663-73. doi: 10.1093/jxb/erq179. [PMID: 20558569]
  • Daniele Del Rio, Angelique Stalmach, Luca Calani, Alan Crozier. Bioavailability of coffee chlorogenic acids and green tea flavan-3-ols. Nutrients. 2010 08; 2(8):820-33. doi: 10.3390/nu2080820. [PMID: 22254058]
  • John H Grabber, Paul F Schatz, Hoon Kim, Fachuang Lu, John Ralph. Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability. BMC plant biology. 2010 Jun; 10(?):114. doi: 10.1186/1471-2229-10-114. [PMID: 20565789]
  • Carolina G Fernandes, Guilhian Leipnitz, Bianca Seminotti, Alexandre U Amaral, Angela Zanatta, Carmen R Vargas, Carlos S Dutra Filho, Moacir Wajner. Experimental evidence that phenylalanine provokes oxidative stress in hippocampus and cerebral cortex of developing rats. Cellular and molecular neurobiology. 2010 Mar; 30(2):317-26. doi: 10.1007/s10571-009-9455-6. [PMID: 19774456]
  • Hiroshi Maeda, Ajit K Shasany, Jennifer Schnepp, Irina Orlova, Goro Taguchi, Bruce R Cooper, David Rhodes, Eran Pichersky, Natalia Dudareva. RNAi suppression of Arogenate Dehydratase1 reveals that phenylalanine is synthesized predominantly via the arogenate pathway in petunia petals. The Plant cell. 2010 Mar; 22(3):832-49. doi: 10.1105/tpc.109.073247. [PMID: 20215586]
  • Harleen Kaur, Nicolas Heinzel, Mathias Schöttner, Ian T Baldwin, Ivan Gális. R2R3-NaMYB8 regulates the accumulation of phenylpropanoid-polyamine conjugates, which are essential for local and systemic defense against insect herbivores in Nicotiana attenuata. Plant physiology. 2010 Mar; 152(3):1731-47. doi: 10.1104/pp.109.151738. [PMID: 20089770]
  • ". Genome sequence of the pea aphid Acyrthosiphon pisum. PLoS biology. 2010 Feb; 8(2):e1000313. doi: 10.1371/journal.pbio.1000313. [PMID: 20186266]
  • Belén Max, José Manuel Salgado, Sandra Cortés, José Manuel Domínguez. Extraction of phenolic acids by alkaline hydrolysis from the solid residue obtained after prehydrolysis of trimming vine shoots. Journal of agricultural and food chemistry. 2010 Feb; 58(3):1909-17. doi: 10.1021/jf903441d. [PMID: 20000463]
  • Rogelio Santiago, Rosa A Malvar. Role of dehydrodiferulates in maize resistance to pests and diseases. International journal of molecular sciences. 2010 Feb; 11(2):691-703. doi: 10.3390/ijms11020691. [PMID: 20386661]
  • Itay Gonda, Einat Bar, Vitaly Portnoy, Shery Lev, Joseph Burger, Arthur A Schaffer, Ya'akov Tadmor, Shimon Gepstein, James J Giovannoni, Nurit Katzir, Efraim Lewinsohn. Branched-chain and aromatic amino acid catabolism into aroma volatiles in Cucumis melo L. fruit. Journal of experimental botany. 2010 Feb; 61(4):1111-23. doi: 10.1093/jxb/erp390. [PMID: 20065117]
  • Fernando Piston, Cristobal Uauy, Lianhai Fu, James Langston, John Labavitch, Jorge Dubcovsky. Down-regulation of four putative arabinoxylan feruloyl transferase genes from family PF02458 reduces ester-linked ferulate content in rice cell walls. Planta. 2010 Feb; 231(3):677-91. doi: 10.1007/s00425-009-1077-1. [PMID: 20012086]
  • Vered Tzin, Gad Galili. The Biosynthetic Pathways for Shikimate and Aromatic Amino Acids in Arabidopsis thaliana. The arabidopsis book. 2010; 8(?):e0132. doi: 10.1199/tab.0132. [PMID: 22303258]
  • Pranav R Prabhu, André O Hudson. Identification and Partial Characterization of an L-Tyrosine Aminotransferase (TAT) from Arabidopsis thaliana. Biochemistry research international. 2010; 2010(?):549572. doi: 10.1155/2010/549572. [PMID: 21188077]
  • Raja S Payyavula, Benjamin A Babst, Matthew P Nelsen, Scott A Harding, Chung-Jui Tsai. Glycosylation-mediated phenylpropanoid partitioning in Populus tremuloides cell cultures. BMC plant biology. 2009 Dec; 9(?):151. doi: 10.1186/1471-2229-9-151. [PMID: 20040108]
  • Tsutomu Aohara, Toshihisa Kotake, Yasuko Kaneko, Hiroshi Takatsuji, Yoichi Tsumuraya, Shinji Kawasaki. Rice BRITTLE CULM 5 (BRITTLE NODE) is involved in secondary cell wall formation in the sclerenchyma tissue of nodes. Plant & cell physiology. 2009 Nov; 50(11):1886-97. doi: 10.1093/pcp/pcp133. [PMID: 19812064]
  • Vered Tzin, Sergey Malitsky, Asaph Aharoni, Gad Galili. Expression of a bacterial bi-functional chorismate mutase/prephenate dehydratase modulates primary and secondary metabolism associated with aromatic amino acids in Arabidopsis. The Plant journal : for cell and molecular biology. 2009 Oct; 60(1):156-67. doi: 10.1111/j.1365-313x.2009.03945.x. [PMID: 19508381]
  • Angélique Stalmach, William Mullen, Denis Barron, Kenichi Uchida, Takao Yokota, Christophe Cavin, Heike Steiling, Gary Williamson, Alan Crozier. Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption. Drug metabolism and disposition: the biological fate of chemicals. 2009 Aug; 37(8):1749-58. doi: 10.1124/dmd.109.028019. [PMID: 19460943]
  • Neil Sidell, Lijuan Hao, Marzia Pasquali, J David McDonald. Carcinogenic effects in a phenylketonuria mouse model. PloS one. 2009; 4(1):e4292. doi: 10.1371/journal.pone.0004292. [PMID: 19172175]
  • David C Dorman, Melanie F Struve, Amy Norris, Alan J Higgins. Metabolomic analyses of body fluids after subchronic manganese inhalation in rhesus monkeys. Toxicological sciences : an official journal of the Society of Toxicology. 2008 Nov; 106(1):46-54. doi: 10.1093/toxsci/kfn159. [PMID: 18684773]
  • Ying-Chun Wong, Ming Zhao, Yu-Ying Zong, Chiu-Yeung Chan, Chun-Tao Che. [Chemical constituents and anti-tuberculosis activity of root of Rhodiola kirilowii]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2008 Jul; 33(13):1561-5. doi: ". [PMID: 18837315]
  • Tetsuya Yamada, Fumio Matsuda, Koji Kasai, Shuichi Fukuoka, Keisuke Kitamura, Yuzuru Tozawa, Hisashi Miyagawa, Kyo Wakasa. Mutation of a rice gene encoding a phenylalanine biosynthetic enzyme results in accumulation of phenylalanine and tryptophan. The Plant cell. 2008 May; 20(5):1316-29. doi: 10.1105/tpc.107.057455. [PMID: 18487352]
  • Jake Stout, Ethan Romero-Severson, Max O Ruegger, Clint Chapple. Semidominant mutations in reduced epidermal fluorescence 4 reduce phenylpropanoid content in Arabidopsis. Genetics. 2008 Apr; 178(4):2237-51. doi: 10.1534/genetics.107.083881. [PMID: 18430946]
  • Isabelle Pontais, Dieter Treutter, Jean-Pierre Paulin, Marie-Noëlle Brisset. Erwinia amylovora modifies phenolic profiles of susceptible and resistant apple through its type III secretion system. Physiologia plantarum. 2008 Mar; 132(3):262-71. doi: 10.1111/j.1399-3054.2007.01004.x. [PMID: 18275458]
  • János Garai, Valéria Molnár, Dániel Eros, László Orfi, Tamás Lóránd. MIF tautomerase inhibitor potency of alpha,beta-unsaturated cyclic ketones. International immunopharmacology. 2007 Dec; 7(13):1741-6. doi: 10.1016/j.intimp.2007.09.014. [PMID: 17996684]
  • A Hargreaves, F A Taiwo, O Duggan, S H Kirk, S I Ahmad. Near-ultraviolet photolysis of beta-phenylpyruvic acid generates free radicals and results in DNA damage. Journal of photochemistry and photobiology. B, Biology. 2007 Dec; 89(2-3):110-6. doi: 10.1016/j.jphotobiol.2007.09.007. [PMID: 17977740]
  • Serena C Marks, William Mullen, Alan Crozier. Flavonoid and hydroxycinnamate profiles of english apple ciders. Journal of agricultural and food chemistry. 2007 Oct; 55(21):8723-30. doi: 10.1021/jf071155u. [PMID: 17867635]
  • Maarten Fauvart, Kristien Braeken, Ruth Daniels, Karen Vos, Maxime Ndayizeye, Jean-Paul Noben, Johan Robben, Jos Vanderleyden, Jan Michiels. Identification of a novel glyoxylate reductase supports phylogeny-based enzymatic substrate specificity prediction. Biochimica et biophysica acta. 2007 Sep; 1774(9):1092-8. doi: 10.1016/j.bbapap.2007.06.009. [PMID: 17693143]
  • Gregory Kaler, David M Truong, Akash Khandelwal, Megha Nagle, Satish A Eraly, Peter W Swaan, Sanjay K Nigam. Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. The Journal of biological chemistry. 2007 Aug; 282(33):23841-53. doi: 10.1074/jbc.m703467200. [PMID: 17553798]
  • Wim Versées, Stijn Spaepen, Jos Vanderleyden, Jan Steyaert. The crystal structure of phenylpyruvate decarboxylase from Azospirillum brasilense at 1.5 A resolution. Implications for its catalytic and regulatory mechanism. The FEBS journal. 2007 May; 274(9):2363-75. doi: 10.1111/j.1742-4658.2007.05771.x. [PMID: 17403037]
  • Irina Orlova, Amy Marshall-Colón, Jennifer Schnepp, Barbara Wood, Marina Varbanova, Eyal Fridman, Joshua J Blakeslee, Wendy Ann Peer, Angus S Murphy, David Rhodes, Eran Pichersky, Natalia Dudareva. Reduction of benzenoid synthesis in petunia flowers reveals multiple pathways to benzoic acid and enhancement in auxin transport. The Plant cell. 2006 Dec; 18(12):3458-75. doi: 10.1105/tpc.106.046227. [PMID: 17194766]
  • Rosario Zamora, José L Navarro, Emerenciana Gallardo, Francisco J Hidalgo. Chemical conversion of alpha-amino acids into alpha-keto acids by 4,5-epoxy-2-decenal. Journal of agricultural and food chemistry. 2006 Aug; 54(16):6101-5. doi: 10.1021/jf061239n. [PMID: 16881723]
  • Vincent M Purpero, Graham R Moran. Catalytic, noncatalytic, and inhibitory phenomena: kinetic analysis of (4-hydroxyphenyl)pyruvate dioxygenase from Arabidopsis thaliana. Biochemistry. 2006 May; 45(19):6044-55. doi: 10.1021/bi052409c. [PMID: 16681377]
  • Kevin T Watts, Pyung C Lee, Claudia Schmidt-Dannert. Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. BMC biotechnology. 2006 Mar; 6(?):22. doi: 10.1186/1472-6750-6-22. [PMID: 16551366]
  • Morando Soffritti, Fiorella Belpoggi, Davide Degli Esposti, Luca Lambertini, Eva Tibaldi, Anna Rigano. First experimental demonstration of the multipotential carcinogenic effects of aspartame administered in the feed to Sprague-Dawley rats. Environmental health perspectives. 2006 Mar; 114(3):379-85. doi: 10.1289/ehp.8711. [PMID: 16507461]
  • Katherine Mary Warpeha, Syed Salman Lateef, Yevgeniya Lapik, Marybeth Anderson, Bao-Shiang Lee, Lon Seth Kaufman. G-protein-coupled receptor 1, G-protein Galpha-subunit 1, and prephenate dehydratase 1 are required for blue light-induced production of phenylalanine in etiolated Arabidopsis. Plant physiology. 2006 Mar; 140(3):844-55. doi: 10.1104/pp.105.071282. [PMID: 16415218]
  • Chung-Jui Tsai, Scott A Harding, Timothy J Tschaplinski, Richard L Lindroth, Yinan Yuan. Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus. The New phytologist. 2006; 172(1):47-62. doi: 10.1111/j.1469-8137.2006.01798.x. [PMID: 16945088]
  • Valeria Molnar, János Garai. Plant-derived anti-inflammatory compounds affect MIF tautomerase activity. International immunopharmacology. 2005 May; 5(5):849-56. doi: 10.1016/j.intimp.2004.12.017. [PMID: 15778121]
  • Arthur J L Cooper. The role of glutamine transaminase K (GTK) in sulfur and alpha-keto acid metabolism in the brain, and in the possible bioactivation of neurotoxicants. Neurochemistry international. 2004 Jun; 44(8):557-77. doi: 10.1016/j.neuint.2003.12.002. [PMID: 15016471]
  • Anne Neudörffer, Dominique Bonnefont-Rousselot, Alain Legrand, Maurice-Bernard Fleury, Martine Largeron. 4-hydroxycinnamic ethyl ester derivatives and related dehydrodimers: Relationship between oxidation potential and protective effects against oxidation of low-density lipoproteins. Journal of agricultural and food chemistry. 2004 Apr; 52(7):2084-91. doi: 10.1021/jf035068n. [PMID: 15053556]
  • János Garai, Herman Adlercreutz. Estrogen-inducible uterine flavonoid binding sites: is it time to reconsider?. The Journal of steroid biochemistry and molecular biology. 2004 Apr; 88(4-5):377-81. doi: 10.1016/j.jsbmb.2004.01.001. [PMID: 15145447]
  • Silvina B Lotito, Balz Frei. Relevance of apple polyphenols as antioxidants in human plasma: contrasting in vitro and in vivo effects. Free radical biology & medicine. 2004 Jan; 36(2):201-11. doi: 10.1016/j.freeradbiomed.2003.10.005. [PMID: 14744632]
  • B Rücker, J P Oses, I B Kirst, S L Berti, C D Bonan, A M O Battastini, J J F Sarkis. Effects of phenylalanine and phenylpyruvate on ATP-ADP hydrolysis by rat blood serum. Amino acids. 2003 Jun; 24(4):383-8. doi: 10.1007/s00726-002-0345-1. [PMID: 12768500]
  • Shawn E Christ. Asbjørn Følling and the discovery of phenylketonuria. Journal of the history of the neurosciences. 2003 Mar; 12(1):44-54. doi: 10.1076/jhin.12.1.44.13788. [PMID: 12785112]
  • Angeles Dios, Robert A Mitchell, Bayan Aljabari, Jodi Lubetsky, KerryAnn O'Connor, Hong Liao, Peter D Senter, Kirk R Manogue, Elias Lolis, Christine Metz, Richard Bucala, David J E Callaway, Yousef Al-Abed. Inhibition of MIF bioactivity by rational design of pharmacological inhibitors of MIF tautomerase activity. Journal of medicinal chemistry. 2002 Jun; 45(12):2410-6. doi: 10.1021/jm010534q. [PMID: 12036350]
  • Scott A Harding, Jacqueline Leshkevich, Vincent L Chiang, Chung-Jui Tsai. Differential substrate inhibition couples kinetically distinct 4-coumarate:coenzyme a ligases with spatially distinct metabolic roles in quaking aspen. Plant physiology. 2002 Feb; 128(2):428-38. doi: 10.1104/pp.010603. [PMID: 11842147]
  • A Kawaoka, H Ebinuma. Transcriptional control of lignin biosynthesis by tobacco LIM protein. Phytochemistry. 2001 Aug; 57(7):1149-57. doi: 10.1016/s0031-9422(01)00054-1. [PMID: 11430987]
  • X Fu, M Kimura, M Iga, S Yamaguchi. Gas chromatographic-mass spectrometric screening for organic acidemias using dried urine filter paper: determination of alpha-ketoacids. Journal of chromatography. B, Biomedical sciences and applications. 2001 Jul; 758(1):87-94. doi: 10.1016/s0378-4347(01)00101-3. [PMID: 11482739]
  • E Larsen, M F Andreasen, L P Christensen. Regioselective dimerization of ferulic acid in a micellar solution. Journal of agricultural and food chemistry. 2001 Jul; 49(7):3471-5. doi: 10.1021/jf0014617. [PMID: 11453793]
  • A R Rechner, J P Spencer, G Kuhnle, U Hahn, C A Rice-Evans. Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free radical biology & medicine. 2001 Jun; 30(11):1213-22. doi: 10.1016/s0891-5849(01)00506-8. [PMID: 11368919]
  • P Cremin, S Kasim-Karakas, A L Waterhouse. LC/ES-MS detection of hydroxycinnamates in human plasma and urine. Journal of agricultural and food chemistry. 2001 Apr; 49(4):1747-50. doi: 10.1021/jf000764y. [PMID: 11308321]
  • A Lomascolo, M Asther, D Navarro, C Antona, M Delattre, L Lesage-Meessen. Shifting the biotransformation pathways of L-phenylalanine into benzaldehyde by Trametes suaveolens CBS 334.85 using HP20 resin. Letters in applied microbiology. 2001 Apr; 32(4):262-7. doi: 10.1046/j.1472-765x.2001.0873a.x. [PMID: 11298938]
  • J P Infante, V A Huszagh. Impaired arachidonic (20:4n-6) and docosahexaenoic (22:6n-3) acid synthesis by phenylalanine metabolites as etiological factors in the neuropathology of phenylketonuria. Molecular genetics and metabolism. 2001 Mar; 72(3):185-98. doi: 10.1006/mgme.2001.3148. [PMID: 11243724]
  • J E Manning Fox, D Meredith, A P Halestrap. Characterisation of human monocarboxylate transporter 4 substantiates its role in lactic acid efflux from skeletal muscle. The Journal of physiology. 2000 Dec; 529 Pt 2(?):285-93. doi: 10.1111/j.1469-7793.2000.00285.x. [PMID: 11101640]
  • G M Fischer, B Nemeti, V Farkas, B Debreceni, A Laszlo, Z Schaffer, C Somogyi, A Sandor. Metabolism of carnitine in phenylacetic acid-treated rats and in patients with phenylketonuria. Biochimica et biophysica acta. 2000 Jun; 1501(2-3):200-10. doi: 10.1016/s0925-4439(00)00023-5. [PMID: 10838193]
  • P Jezek, J Borecký. Mitochondrial uncoupling protein may participate in futile cycling of pyruvate and other monocarboxylates. The American journal of physiology. 1998 08; 275(2):C496-504. doi: 10.1152/ajpcell.1998.275.2.c496. [PMID: 9688604]
  • A El Sawalhy, J R Seed, J E Hall, H El Attar. Increased excretion of aromatic amino acid catabolites in animals infected with Trypanosoma brucei evansi. The Journal of parasitology. 1998 Jun; 84(3):469-73. doi: . [PMID: 9645841]
  • Kh K Karshiev. [Effects of ultraviolet irradiation of blood and sodium hypochlorite on aromatic amino acid metabolism in phlegmons of the maxillofacial region]. Vestnik khirurgii imeni I. I. Grekova. 1998; 157(6):72-3. doi: NULL. [PMID: 10672668]
  • I B Ostretsova, A A Nikiforov. Weak organic acid uptake in rat renal tubules in vitro: stimulation by pent-4-enoic acid. Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology. 1997 May; 117(1):1-6. doi: 10.1016/s0742-8413(96)00200-9. [PMID: 9185322]
  • A T Wyse, M Wajner, A Brusque, C M Wannmacher. Alanine reverses the inhibitory effect of phenylalanine and its metabolites on Na+,K(+)-ATPase in synaptic plasma membranes from cerebral cortex of rats. Biochemical Society transactions. 1995 May; 23(2):227S. doi: 10.1042/bst023227s. [PMID: 7672247]
  • A A Nikiforov, I B Ostretsova. Stimulation of weak organic acid uptake in rat renal tubules by cadmium and nystatin. Biochemical pharmacology. 1994 Mar; 47(5):815-20. doi: 10.1016/0006-2952(94)90481-2. [PMID: 8135857]