Comparison between a Biochemical Pathway and Organic Chemical Synthesis

Journal Title: Archives of Organic and Inorganic Chemical Sciences - Year 2018, Vol 2, Issue 2

Abstract

The first reaction of biochemical degradation pathway from L-phenylalanine to L-tyrosine (para-hydroxy-L-phenylalanine) is compared with organic chemical synthesis of ortho-hydroxy-L- phenylalanine, meta-hydroxy-L-phenylalanine and para-hydroxy- L-phenylalanine. Enzymatic reaction is specific for the para- isomer, is a quicker reaction and shows higher yield than non enzymatic reactions. L-Tyrosine (Tyr or Y), or 4-hydroxy L-phenylalanine (para- hydroxy-L-phenylalanine) is one of the 20 standard amino acids used in protein synthesis. In humans, L-phenylalanine is an indispensable dietary amino acid. Nevertheless, L-tyrosine is not considered an indispensable dietary amino acid for humans, as it can be synthesized from L-phenylalanine in the first reaction of L-phenylalanine degradation. This reaction is enzymatically catalyzed by phenylalanine-4-hydroxylase (E.C. 1.14.16.1.), and this enzyme is located in the cytosol and expressed predominantly in the liver and kidney [1]. Mammalian phenylalanine-4-hydroxylase uses (6R)-tetrahydrobiopterin as a cofactor [2] in a reaction mechanism shown in Figure 1. In mammals, L-tyrosine is precursor of neurotransmitters and hormones. In dopaminergic cells in brain this amino acid is converted to L-DOPA (3,4-dihydroxy L-phenylalanine) and dopamine (3,4-dihydroxy phenethylamine) and furthermore to cathecolamines, such as noradrenaline (norepinephrine) and adrenaline (epinephrine). Thyroid hormones derived from L-tyrosine are triiodothyronine (T3) and thyroxine (T4). L-tyrosine is also precursor of alkaloids in plants (including morphine and mescaline), natural phenols derived from p-coumaric acid, pigments (including melanin) and the benzoquinone structure of coenzyme Q. Thus, due to the interest of L-tyrosine as precursor of the previous described compounds, industrial synthesis of L-tyrosine and its derivatives has been performed. L-DOPA, melanin, phenylpropanoids and others compounds are used in pharmaceuticals, dietary supplements and food additives. Biochemical pathways consist in metabolic transformations to obtain a final product. Enzymes are chiral molecules, as they are formed from L-amino acids. Thus, they can catalyze organic reactions allowing generation of chiral compounds.

Authors and Affiliations

Josep J Centelles

Keywords

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  • EP ID EP602960
  • DOI 10.32474/AOICS.2018.02.000132
  • Views 72
  • Downloads 0

How To Cite

Josep J Centelles (2018). Comparison between a Biochemical Pathway and Organic Chemical Synthesis. Archives of Organic and Inorganic Chemical Sciences, 2(2), 165-167. https://europub.co.uk/articles/-A-602960