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Understanding Tryptophan: Chemical Properties, Sources, and Biological Significance

Tryptophan, an essential amino acid with a molecular formula of C11H12N2O2 and a molecular weight of 204.23, plays a vital role in human health. It is crucial for synthesizing serotonin and melatonin, neurotransmitters that help regulate mood and sleep. Found in various foods such as bananas, milk, and fish, tryptophan is known for its effectiveness as a sleep aid and its potential in treating emotional disorders. Additionally, it's a precursor for vitamin B3 and plant growth hormones. This article delves into the biosynthesis and regulatory mechanisms of tryptophan.

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Understanding Tryptophan: Chemical Properties, Sources, and Biological Significance

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  1. Team ProjectChemicals- Tryptophan 組員： 林瑋耿, 吳東耘, 許博凱, 彭嘉冠 System Biology

  2. Tryptophan • Molecular formula • C11H12N2O2 • Molecular weight • 204.23 • Isoelectric point • pH 5.89 • CAS number • 73-22-3 Functional group : indole System Biology

  3. Where to get it ? • Tryptophan was available in health food • Banana, milk, fish, and etc. … System Biology

  4. What are its usage ? • Tryptophan is effective sleep aid. • It shows considerable promise as an antidepressant. • Other promising indications include reduce some emotional disorders. • Impulsive, violent, and etc. disorders System Biology

  5. Cont. • 人類必需胺基酸之一種 (無法自行合成) • 合成serotonin的原料, 是神經傳導物質之一種, 能抑制食慾產生飽足感 • 合成melatonin的原料, 能幫助睡眠, 安定心情, 增強免疫力, 常被用來調整時差 • Serotonin和melatonin的量會隨著日夜而波動, 推測與生理時鐘的調節有關 • 維生素B3 (菸鹼酸, niacin) 的原料, 作為輔脢 (coenzyme) 幫助代謝作用進行 • 植物生長激素IAA (auxin) 的原料 System Biology

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  8. NAD+ & NADH 2e- + 2H+ System Biology

  9. Tryptophan Biosynthesis System Biology

  10. Inhibited by L-tryptophan 1 Inhibited by L-tyrosine Inhibited by L-phenyalanine 2 3 4 5 1- Phospho-2-dehydro-3-deoxyheptonate aldolase [EC:2.5.1.54] 2- 3-dehydroquinate synthase [EC:4.2.3.4] 3- 3-dehydroquinate dehydratase (3-dehydroquinase)[EC:4.2.1.10] Enolase[EC:4.2.1.11] 4- shikimate 5-dehydrogenase [EC:1.1.1.25] 5- shikimate kinase II (SKII) [EC:2.7.1.71] 6- 3-phosphoshikimate 1-carboxyvinyltransferase [EC:2.5.1.19] 7- chorismate synthase [EC:4.2.3.5] 6 7 System Biology

  11. 9 Inhibited by L-tryptophan 8 11 10 8 & 9- anthranilate phosphoribosyltransferase / anthranilate synthasecomponent II [EC:2.4.2.18, 4.1.3.27] 10 & 11- indole-3-glycerol phosphate synthase (IGPS) /N-(5'-phospho-ribosyl)anthranilate isomerase (PRAI) [EC:4.1.1.48,5.3.1.24] 12- tryptophan synthase [EC:4.2.1.20] 12 System Biology

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  13. Tryptophan operon in E.coli trpD + trpE = enzyme 8 & 9 trpC = enzyme 10 & 11 trpA + trpB = enzyme 12 Control the 5 reactions from chorismate to tryptophan !! System Biology

  14. Trp operon mechanism System Biology

  15. References • KEGG: http://www.genome.jp/kegg/ • EcoCyc: http://www.ecocyc.com/ • free encyclopedia: http://en.wikipedia.org/wiki/Main_Page System Biology

  16. The End System Biology

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