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Pyridoxal phosphate information


Pyridoxal phosphate
Skeletal formula
Idealised skeletal formula
Ball-and-stick model
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.
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
Identifiers
CAS Number
  • 54-47-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18405
ChEMBL
  • ChEMBL82202 ☒N
ECHA InfoCard 100.000.190 Edit this at Wikidata
IUPHAR/BPS
  • 5249
MeSH Pyridoxal+Phosphate
PubChem CID
  • 1051
UNII
  • F06SGE49M6 checkY
CompTox Dashboard (EPA)
  • DTXSID4048351 Edit this at Wikidata
SMILES
  • O=Cc1c(O)c(C)ncc1COP(O)(O)=O
Properties
Chemical formula
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
ATC code
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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Infobox references

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.

  1. ^ "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.
  2. ^ 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.
  3. ^ a b c Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (© 1994-2011 ACD/Labs)
  4. ^ 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.
  5. ^ 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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Pyridoxal phosphate

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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...

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Zwitterion

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gained from the results of theoretical calculations. For example, pyridoxal phosphate, a form of vitamin B6, in aqueous solution is predicted to have an...

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Transsulfuration pathway

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transsulfuration enzymes require vitamin B6 in its active form (pyridoxal phosphate or PLP). Three of these enzymes (cystathionine γ-synthase excluded)...

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Aspartate transaminase

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AspAT/ASAT/AAT or (serum) glutamic oxaloacetic transaminase (GOT, SGOT), is a pyridoxal phosphate (PLP)-dependent transaminase enzyme (EC 2.6.1.1) that was first described...

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Pyridoxal

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9 billion years ago, a forerunner of the Great Oxidation Event. Pyridoxal phosphate "CSD Entry: BIHKEI01". Cambridge Structural Database: Access Structures...

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Melatonin

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(5-HTP). Subsequently, 5-HTP undergoes decarboxylation, facilitated by pyridoxal phosphate and the enzyme 5-hydroxytryptophan decarboxylase, yielding serotonin...

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Alanine transaminase

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L-glutamate ALT (and all aminotransferases) require the coenzyme pyridoxal phosphate, which is converted into pyridoxamine in the first phase of the reaction...

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Prosthetic group

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prosthetic groups are vitamin derivatives: thiamine pyrophosphate, pyridoxal-phosphate and biotin. Since prosthetic groups are often vitamins or made from...

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Transaminase

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amino acid.[citation needed] Transaminases require the coenzyme pyridoxal phosphate, which is converted into pyridoxamine in the first half-reaction...

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Imine

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reaction and Kabachnik–Fields reaction Imines are common in nature. The pyridoxal phosphate-dependent enzymes (PLP enzymes) catalyze myriad reactions involving...

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Methionine

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PLP-dependent fold type I clade. They utilise the cofactor PLP (pyridoxal phosphate), which functions by stabilising carbanion intermediates. If it reacts...

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Tautomer

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nucleobases guanine, thymine, and cytosine imine – imine, e.g., during pyridoxal phosphate catalyzed enzymatic reactions R1R2C(=NCHR3R4) ⇌ (R1R2CHN=)CR3R4 nitro...

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Vitamin B6

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which can be interconverted in biological systems. Its active form, pyridoxal 5′-phosphate, serves as a coenzyme in more than 140 enzyme reactions in amino...

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Decarboxylation

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RC(O)CO2H → T=C(OH)R + CO2 T=C(OH)R + R'COOH → T! : + RC(O)CH(OH)R' Pyridoxal phosphate promotes decarboxylation of amino acids. Flavin-dependent decarboxylases...

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Tyrosine aminotransferase

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pyridoxal phosphate (right), and the resulting product 4-hydroxyphenylpyruvate (center). Each side of the dimer protein includes pyridoxal phosphate (PLP)...

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Serine dehydratase

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dehydratase or L-serine ammonia lyase (SDH) is in the β-family of pyridoxal phosphate-dependent (PLP) enzymes. SDH is found widely in nature, but its structure...

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Glutamate decarboxylase

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gamma-aminobutyric acid (GABA) and carbon dioxide (CO2). GAD uses pyridoxal-phosphate (PLP) as a cofactor. The reaction proceeds as follows: HOOC−CH2−CH2−CH(NH2)−COOH...

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Allicin

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gives the sulfoxide (alliin). The enzyme alliinase, which contains pyridoxal phosphate (PLP), cleaves alliin, generating allylsulfenic acid (CH2=CHCH2SOH)...

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Tryptophan synthase

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irreversible condensation of indole and serine to form tryptophan in a pyridoxal phosphate (PLP) dependent reaction. Each α active site is connected to a β...

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Norepinephrine

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L-amino acid decarboxylase (also known as DOPA decarboxylase), with pyridoxal phosphate as a cofactor. Dopamine is then converted into norepinephrine by...

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Serine hydroxymethyltransferase

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Serine hydroxymethyltransferase (SHMT) is a pyridoxal phosphate (PLP) (Vitamin B6) dependent enzyme (EC 2.1.2.1) which plays an important role in cellular...

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Pyridoxal kinase

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+ pyridoxal 5'-phosphate Thus, the two substrates of this enzyme are ATP and pyridoxal, whereas its two products are ADP and pyridoxal 5'-phosphate. This...

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