2226-71-3
Chemical Structure
4’-Phosphopantetheine
- CAS No.: 2226-71-3
- Formula:C11H23N2O7PS
- Molecular Weight:358.35
InChIKey: JDMUPRLRUUMCTL-VIFPVBQESA-N
SMILES: SCCNC(CCNC([C@H](O)C(C)(C)COP(O)(O)=O)=O)=O
Biological Activity: 4’-Phosphopantetheine is an orally active coenzyme A (CoA) precursor. 4’-Phosphopantetheine is membrane-permeable and acts as a CoA precursor, a prosthetic group, and a reactive oxygen species (ROS) inhibitor. 4’-Phosphopantetheine binds covalently to rat liver fatty acid synthase, modifies the conserved serine residue in the PKS/NRPS carrier protein domain, and serves as a substrate for CoA synthase and PPAT. 4’-Phosphopantetheine undergoes non-catalytic exchange on rat liver fatty acid synthase, with a faster turnover rate than that of the enzyme complex, and restores intracellular CoA levels in cells with impaired de novo biosynthesis. 4’-Phosphopantetheine rescues phenotypes induced by CoA deficiency, normalizes PKAN-related biomarkers, restores mitochondrial enzyme activity, and alleviates vascular endothelial damage. 4’-Phosphopantetheine shows biological stability in serum, acts as a prosthetic group and degradation product of ACP, and inhibits the formation of atherosclerotic plaques. 4’-Phosphopantetheine can be used in the research of brain iron accumulation neurodegenerative diseases, pantothenate kinase-associated neurodegeneration, CoASY protein-associated neurodegenerative diseases, coronary heart disease, and atherosclerosis[1][2][3][4][5][6][7][8].
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4’-Phosphopantetheine | 4’-Phosphopantetheine is an orally active coenzyme A (CoA) precursor. 4’-Phosphopantetheine is membrane-permeable and acts as a CoA precursor, a prosthetic group, and a reactive oxygen species (ROS) inhibitor. 4’-Phosphopantetheine binds covalently to rat liver fatty acid synthase, modifies the conserved serine residue in the PKS/NRPS carrier protein domain, and serves as a substrate for CoA synthase and PPAT. 4’-Phosphopantetheine undergoes non-catalytic exchange on rat liver fatty acid synthase, with a faster turnover rate than that of the enzyme complex, and restores intracellular CoA levels in cells with impaired de novo biosynthesis. 4’-Phosphopantetheine rescues phenotypes induced by CoA deficiency, normalizes PKAN-related biomarkers, restores mitochondrial enzyme activity, and alleviates vascular endothelial damage. 4’-Phosphopantetheine shows biological stability in serum, acts as a prosthetic group and degradation product of ACP, and inhibits the formation of atherosclerotic plaques. 4’-Phosphopantetheine can be used in the research of brain iron accumulation neurodegenerative diseases, pantothenate kinase-associated neurodegeneration, CoASY protein-associated neurodegenerative diseases, coronary heart disease, and atherosclerosis. | |||||||||||||||||||||
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- [1]. Tweto J, et al. Protein turnover and 4'-phosphopantetheine exchange in rat liver fatty acid synthetase. J Biol Chem. 1971 Apr 25;246(8):2468-71. [Content Brief]
- [2]. Srinivasan B, et al. Extracellular 4'-phosphopantetheine is a source for intracellular coenzyme A synthesis. Nature chemical biology. 2015 Oct;11(10):784-92. [Content Brief]
- [3]. Jeong SY, et al. 4'-Phosphopantetheine corrects CoA, iron, and dopamine metabolic defects in mammalian models of PKAN. EMBO molecular medicine. 2019 Dec;11(12):e10489. [Content Brief]
- [4]. MAJERUS PW, et al. ACYL CARRIER PROTEIN. IV. THE IDENTIFICATION OF 4'-PHOSPHOPANTETHEINE AS THE PROSTHETIC GROUP OF THE ACYL CARRIER PROTEIN. Proc Natl Acad Sci U S A. 1965 Feb;53(2):410-7. [Content Brief]
- [5]. Jackowski S, et al. Metabolism of 4'-phosphopantetheine in Escherichia coli. Journal of bacteriology. 1984 Apr;158(1):115-20. [Content Brief]
- [6]. Meier JL, et al. Practical 4'-phosphopantetheine active site discovery from proteomic samples. Journal of proteome research. 2011 Jan 07;10(1):320-9. [Content Brief]
- [7]. de Jonge BL, et al. Discovery of inhibitors of 4'-phosphopantetheine adenylyltransferase (PPAT) to validate PPAT as a target for antibacterial therapy. Antimicrobial agents and chemotherapy. 2013 Dec;57(12):6005-15. [Content Brief]
- [8]. Zhai T, et al. 4'-phosphopantetheine acts as a potential antioxidant to limit atherosclerotic plaque formation by inhibiting ROS generation. Frontiers in physiology. 2022;13:989105. [Content Brief]
Keywords
