(5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-CoA (BioDeep_00000226357)

描述信息

(5z,8s,9e,11z,14z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (5Z_8S_9E_11Z_14Z)-8-hydroxyicosa-5_9_11_14-tetraenoic acid thioester of coenzyme A. (5z,8s,9e,11z,14z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-coa is an acyl-CoA with 20 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoAs are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. (5z,8s,9e,11z,14z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-coa is therefore classified as a long chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. (5z,8s,9e,11z,14z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-coa, being a long chain acyl-CoA is a substrate for long chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-CoA into (5Z_8S_9E_11Z_14Z)-8-hydroxyicosa-5_9_11_14-tetraenoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (5Z_8S_9E_11Z_14Z)-8-hydroxyicosa-5_9_11_14-tetraenoylcarnitine is converted back to (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoyl-CoA occurs in four steps. First, since (5Z,8S,9E,11Z,14Z)-...

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