{"id":1935,"date":"2020-08-19T13:30:17","date_gmt":"2020-08-19T13:30:17","guid":{"rendered":"https:\/\/meddists.com\/learn\/pre-clinical\/biochemistry\/biochemistry-of-the-metabolism\/amino-acid-metabolism\/monooxygenation-and-dioxygenation-reactions\/"},"modified":"2021-12-12T10:30:05","modified_gmt":"2021-12-12T08:30:05","slug":"monooxygenation-and-dioxygenation-reactions","status":"publish","type":"page","link":"https:\/\/meddists.com\/learn\/pre-clinical\/biochemistry\/biochemistry-of-the-metabolism\/amino-acid-metabolism\/monooxygenation-and-dioxygenation-reactions\/","title":{"rendered":"Monooxygenation and Dioxygenation Reactions"},"content":{"rendered":"\n<p class=\"wp-block-paragraph\"><div class=\"intro\">Oxygenation reactions are the ones in which the molecular oxygen atom is added to another molecule. In most cases, it can open up the ring e.g aromatic amino acids like PHE, TYR, TRP. Based on the fact that O2 has two atoms if both are used the process is called dioxygenation while using one of them is a monooxygenation reaction.<\/div><\/p>\n\n\n<span class=\"block-heading\" id=\"header_1\">\n<h2 class=\"wp-block-heading\" class=\"wp-block-heading\" class=\"title_collection title1\">Monooxygenation<\/h2>\n<\/span><span class=\"block-content\" id=\"contents_1\">\n\n\n<div class=\"wp-block-columns is-layout-flex wp-container-core-columns-is-layout-8f761849 wp-block-columns-is-layout-flex\">\n<div class=\"wp-block-column is-layout-flow wp-block-column-is-layout-flow\">\n<p class=\"wp-block-paragraph\">In monooxygenation, one atom of molecular oxygen forms the hydroxyl group of the substrate while the other forms water with the hydrogens of the cofactor.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">The role of monooxygenation (hydroxylation) in amino acid metabolism:<\/p>\n\n\n\n<ol class=\"wp-block-list\"><li>PHE degradation into TYR<\/li><li>Neurotransmitter synthesis from TYR, TRP<\/li><\/ol>\n\n\n\n<p class=\"wp-block-paragraph\">There is an aromatic amino acid hydroxylase enzyme family: enzymes of this family use tetrahydrobiopterin (BH<sub>4<\/sub>), as a cofactor (Figure 1).<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Important to note, that the BH<sub>4<\/sub>-BH<sub>2<\/sub> circle can recover by the spontaneous way which is really slow or by the BH<sub>2<\/sub> reductase using NADPH. In the non-classical PKU, this reductase is missing.<\/p>\n<\/div>\n\n\n\n<div class=\"wp-block-column is-layout-flow wp-block-column-is-layout-flow\">\n<figure class=\"wp-block-image size-large\"><a href=\"https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20.png\" target=\"_blank\" title=\"Monooxygenation and Dioxygenation Reactions\"><img loading=\"lazy\" decoding=\"async\" width=\"1024\" height=\"686\" src=\"https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20-1024x686.png\" alt=\"\" class=\"wp-image-9082\" srcset=\"https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20-1024x686.png 1024w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20-300x201.png 300w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20-768x514.png 768w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20-1536x1028.png 1536w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA20-2048x1371.png 2048w\" sizes=\"auto, (max-width: 1024px) 100vw, 1024px\" \/><\/a><figcaption><strong>Figure 1. PHE-TYR change using BH4 cofactor<\/strong><\/figcaption><\/figure>\n<\/div>\n<\/div>\n\n\n<\/span><span class=\"block-heading\" id=\"header_2\">\n<h3 class=\"wp-block-heading\" class=\"wp-block-heading\" class=\"title_collection title2\">Phenylalanine hydroxylase<\/h3>\n<\/span><span class=\"block-content\" id=\"contents_2\">\n\n\n<p class=\"wp-block-paragraph\">The reaction occurs only in the direction of tyrosine formation. Dihydrobiopterin is reduced back to BH4 by the dihydrobiopterin reductase.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Mutations in the phenylalanine hydroxylase gene cause classical PKU.<\/p>\n\n\n<\/span><span class=\"block-heading\" id=\"header_3\">\n<h2 class=\"wp-block-heading\" class=\"wp-block-heading\" class=\"title_collection title1\">Deoxygenation reactions<\/h2>\n<\/span><span class=\"block-content\" id=\"contents_3\">\n\n\n<div class=\"wp-block-columns is-layout-flex wp-container-core-columns-is-layout-8f761849 wp-block-columns-is-layout-flex\">\n<div class=\"wp-block-column is-layout-flow wp-block-column-is-layout-flow\" style=\"flex-basis:66.66%\">\n<figure class=\"wp-block-image size-large\"><a href=\"https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1.png\" target=\"_blank\" title=\"Monooxygenation and Dioxygenation Reactions\"><img loading=\"lazy\" decoding=\"async\" width=\"959\" height=\"1024\" src=\"https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1-959x1024.png\" alt=\"\" class=\"wp-image-9100\" srcset=\"https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1-959x1024.png 959w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1-281x300.png 281w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1-768x820.png 768w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1-1439x1536.png 1439w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1-1919x2048.png 1919w, https:\/\/meddists.com\/learn\/wp-content\/uploads\/2021\/12\/AA21-1.png 2000w\" sizes=\"auto, (max-width: 959px) 100vw, 959px\" \/><\/a><figcaption><strong>Figure 2. Degradation of the TYR into Homogentisate<\/strong><\/figcaption><\/figure>\n<\/div>\n\n\n\n<div class=\"wp-block-column is-layout-flow wp-block-column-is-layout-flow\" style=\"flex-basis:33.33%\">\n<p class=\"wp-block-paragraph\">In deoxygenation reactions, both atoms of molecular oxygen enter the substrate. Its role in amino acid metabolism is the opening of aromatic rings.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">In the degradation of PHE and TYR, the ring-opening occurs in the reaction catalysed by homogentisate dioxygenase (Figure 2).<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">For the dioxygenation reaction, the amine group needs to be transferred, this reaction is catalyzed by the TYR transaminase in the presence of the cofactor PLP. <\/p>\n\n\n\n<p class=\"wp-block-paragraph\">Removal of the amine group generates hydroxyphenylpyruvate which is changed into homogentisate with iron and an enzyme called hydroxyphenylpyruvate dioxygenase.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\">The homogentisate changes forward into maleylacetoacetate with another dioxygenase enzyme in the presence of iron respectively.<\/p>\n\n\n\n<p class=\"wp-block-paragraph\"><strong>Alcaptonuria<\/strong> disease develops if the homogentisate dioxygenase is missing.<\/p>\n<\/div>\n<\/div>\n\n\n<\/span><span class=\"block-heading\" id=\"header_4\">\n<h2 class=\"wp-block-heading\" class=\"wp-block-heading\" class=\"title_collection title1\">References<\/h2>\n<\/span><span class=\"block-content\" id=\"contents_4\">\n\n\n<p class=\"wp-block-paragraph\">S<span style=\"font-size: revert; color: initial;\">nider MDS. Devlin\u2019s <strong>Textbook of Biochemistry with Clinical Correlations<\/strong>, the 8th Edition. John Wiley &amp; Sons, Incorporated, 2020; 2019.<\/span>  <\/p>\n<\/span><div id=\"the_titles\" style=\"display:none;\"><h2 class=\"wp-block-heading\" class=\"wp-block-heading\">Monooxygenation<\/h2><h3 class=\"wp-block-heading\" class=\"wp-block-heading\">Phenylalanine hydroxylase<\/h3><h2 class=\"wp-block-heading\" class=\"wp-block-heading\">Deoxygenation reactions<\/h2><h2 class=\"wp-block-heading\" class=\"wp-block-heading\">References<\/h2><\/div>","protected":false},"excerpt":{"rendered":"<p>Monooxygenation In monooxygenation, one atom of molecular oxygen forms the hydroxyl group of the substrate while the other forms water with the hydrogens of the cofactor. The role of monooxygenation (hydroxylation) in amino acid metabolism: PHE degradation into TYR Neurotransmitter synthesis from TYR, TRP There is an aromatic amino acid hydroxylase enzyme family: enzymes of [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"parent":1714,"menu_order":21,"comment_status":"closed","ping_status":"closed","template":"","meta":{"footnotes":""},"class_list":["post-1935","page","type-page","status-publish","hentry"],"yoast_head":"<!-- This site is optimized with the Yoast SEO plugin v27.8 - https:\/\/yoast.com\/product\/yoast-seo-wordpress\/ -->\n<title>Monooxygenation and Dioxygenation Reactions &#8211; Meddists<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/meddists.com\/learn\/pre-clinical\/biochemistry\/biochemistry-of-the-metabolism\/amino-acid-metabolism\/monooxygenation-and-dioxygenation-reactions\/\" \/>\n<meta name=\"twitter:label1\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data1\" content=\"2 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/meddists.com\\\/learn\\\/pre-clinical\\\/biochemistry\\\/biochemistry-of-the-metabolism\\\/amino-acid-metabolism\\\/monooxygenation-and-dioxygenation-reactions\\\/\",\"url\":\"https:\\\/\\\/meddists.com\\\/learn\\\/pre-clinical\\\/biochemistry\\\/biochemistry-of-the-metabolism\\\/amino-acid-metabolism\\\/monooxygenation-and-dioxygenation-reactions\\\/\",\"name\":\"Monooxygenation and Dioxygenation Reactions &#8211; 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