Pantetheine is thecysteamineamideanalog ofpantothenic acid (vitamin B5). The dimer of this compound,pantethine is more commonly known, and is considered to be the most potent form of vitamin B5. Pantetheine is an intermediate in the catabolism ofcoenzyme A by the body.[1][2][3]
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| Names | |
|---|---|
| Systematic IUPAC name (2R)-2,4-Dihydroxy-3,3-dimethyl-N-{3-oxo-3-[(2-sulfanylethyl)amino]propyl}butanamide | |
| Other names Pantetheine | |
| Identifiers | |
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3D model (JSmol) | |
| 1714196R | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.114 |
| EC Number |
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| KEGG |
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| MeSH | Pantetheine |
| UNII |
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| Properties | |
| C11H22N2O4S | |
| Molar mass | 278.37 g·mol−1 |
| Related compounds | |
Related compounds | Pantethine |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Metabolism
editPantetheine is the product ofdephosphorylation ofphosphopantetheine:
- phosphopantetheine → pantetheine + Pi
InE. coli, this reaction is catalyzed by for examplealkaline phosphatase.[4] The reverse reaction, phosphopantetheine synthesis, is catalyzed by variouskinases:[5]
- phosphopantetheine + ATP → pantetheine + ADP
These kinases are able to act uponpantothenoic acid as well and are present in both microorganisms and animal livers.[5]
Pantetheine is degraded bypantetheinase, which splits it intocysteamine andpantothenic acid:[3]
- pantetheine → cysteamine + pantothenate
Prebiotic evolution
editSince pantetheine is a part of coenzyme A, a commoncofactor, it is thought to have been present inprebiotic soup. A synthesis mechanism has also been suggested.[6]
References
edit- ^Hoagland MB, Novelli GD (April 1954)."Biosynthesis of coenzyme A from phospho-pantetheine and of pantetheine from pantothenate".The Journal of Biological Chemistry.207 (2):767–773.doi:10.1016/S0021-9258(18)65696-0.PMID 13163064.
- ^Cronan JE (June 2014). "The chain-flipping mechanism of ACP (acyl carrier protein)-dependent enzymes appears universal".The Biochemical Journal.460 (2):157–163.doi:10.1042/BJ20140239.PMID 24825445.
- ^abNitto T, Onodera K (September 2013)."Linkage between coenzyme a metabolism and inflammation: roles of pantetheinase".Journal of Pharmacological Sciences.123 (1):1–8.doi:10.1254/jphs.13R01CP.PMID 23978960.
- ^Jackowski S, Rock CO (April 1984)."Metabolism of 4'-phosphopantetheine in Escherichia coli".Journal of Bacteriology.158 (1):115–120.doi:10.1128/jb.158.1.115-120.1984.PMC 215387.PMID 6370952.
- ^abBrown GM (1970-01-01), Florkin M, Stotz EH (eds.),"Section d - Biosynthesis of Pantothenic Acid and Coenzyme A",Comprehensive Biochemistry, Metabolism of Vitamins and Trace Elements, vol. 21, Elsevier, pp. 73–80,doi:10.1016/b978-0-444-40871-6.50012-x, retrieved2023-10-29
- ^Keefe AD, Newton GL, Miller SL (February 1995). "A possible prebiotic synthesis of pantetheine, a precursor to coenzyme A".Nature.373 (6516):683–685.Bibcode:1995Natur.373..683K.doi:10.1038/373683a0.PMID 7854449.S2CID 4255864.