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Pyridoxal phosphate
 Idealised skeletal formula
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 Ball-and-stick model based on the crystal structure.[1][2] Note that the phosphate and pyridine groups have reacted to form a zwitterion and the aldehyde group is hydrated.
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| Names | |
|---|---|
| Preferred IUPAC name
(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate | |
| Other names
Pyridoxal 5-phosphate, PAL-P, PLP, Vitamin B6 phosphate
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ECHA InfoCard | 100.000.190 |
| MeSH | Pyridoxal+Phosphate |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C8H10NO6P | |
| Molar mass | 247.142 g/mol |
| Density | 1.638±0.06 g/cm3[3] |
| Melting point | 139 to 142 °C (282 to 288 °F; 412 to 415 K)[4] |
| Acidity (pKa) | 1.56[3] |
| Pharmacology | |
| A11HA06 (WHO) | |
| Hazards | |
| Flash point | 296.0±32.9 °C[3] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyridoxal phosphate (PLP, pyridoxal 5'-phosphate, P5P), the active form of vitamin B6, is a coenzyme in a variety of enzymatic reactions. The International Union of Biochemistry and Molecular Biology has catalogued more than 140 PLP-dependent activities, corresponding to ~4% of all classified activities.[5] The versatility of PLP arises from its ability to covalently bind the substrate, and then to act as an electrophilic catalyst, thereby stabilizing different types of carbanionic reaction intermediates.
- ^ "CSD Entry: PLPHYD10". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. 1974. Archived from the original on 2023-11-04. Retrieved 2023-11-04.
- ^ Fujiwara T (1973). "The Crystal and Molecular Structure of Vitamin B6 Derivatives. I. Pyridoxal Phosphate Hydrate and Pyridoxal Phosphate Methyl Hemiacetal". Bull. Chem. Soc. Jpn. 46 (3): 863–871. doi:10.1246/bcsj.46.863.
- ^ a b c Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2011 ACD/Labs)
- ^ Kozlov ÉI, L'vova MS (1978). "Stability of water-soluble vitamins and coenzymes. Hydrolysis of pyridoxal-5-phosphate in acidic, neutral, and weakly alkaline solutions". Pharmaceutical Chemistry Journal. 11 (11): 1543–9. doi:10.1007/BF00778244. S2CID 1094223.
- ^ Percudani R, Peracchi A (September 2003). "A genomic overview of pyridoxal-phosphate-dependent enzymes". EMBO Reports. 4 (9): 850–4. doi:10.1038/sj.embor.embor914. PMC 1326353. PMID 12949584.
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