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Pyridoxal phosphate

Names
IUPAC name phosphonic acid
Identifiers
CAS Number	54-47-7
3D model (JSmol)	Interactive image
ECHA InfoCard	100.000.190
MeSH	Pyridoxal+Phosphate
PubChem CID	1051
CompTox Dashboard (EPA)	DTXSID4048351
SMILES CC1=NC=C(C(=C1O) C=O)COP(=O)(O)O
Properties
Chemical formula	C8H10NO6P
Molar mass	247.142 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Pyridoxal-phosphate (PLP, pyridoxal-5'-phosphate, P5P) is a prosthetic group of some enzymes. It is the active form of vitamin B₆, which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine.

Role as a coenzyme

PLP acts as a coenzyme in all transamination reactions, and in some decarboxylation and deamination reactions of amino acids. The aldehyde group of PLP forms a Schiff-base linkage (internal aldimine) with the ε-amino group of a specific lysine group of the aminotransferase enzyme. The α-amino group of the amino acid substrate displaces the ε-amino group of the active-site lysine residue. The resulting external aldimine becomes deprotonated to become a quinoid intermediate, which in turn accepts a proton at a different position to become a ketimine. The resulting ketimine is hydrolysed so that the amino group remains on the complex.

In addition, PLP is used by aminotransferases (or transaminases) that act upon unusual sugars such as perosamine and desosamine. In these reactions, the PLP reacts with glutamate, which transfers its alpha-amino group to PLP to make pyridoxamine phosphate (PMP). PMP then transfers its nitrogen to the sugar, making an amino sugar.

PLP is also involved in various beta-elimination reactions such as the reactions carried out by serine dehydratase and GDP-4-keto-6-deoxymannose-3-dehydratase (ColD).

This article contains a list of miscellaneous information. Please relocate any relevant information into other sections or articles. (August 2009)

It is also active in the condensation reaction in heme synthesis.

Pyridoxal phosphate is not required in the transaminase reaction of lysine catabolism.

PLP plays a role in the conversion of Dopa into Dopamine

PLP allows the conversion of the excitatory neurotransmitter Glutamate to the inhibitory neurotransmitter GABA.

PLP also allows SAM to be decarboxylated to form propylamine which is a precursor to polyamines.

PLP allows the conversion of histidine to histamine via decarboxylation.

Non-classical examples of PLP

PLP is also found on glycogen phosphorylase in the liver, where it is used to break down glycogen in glycogenolysis when glucagon or epinephrine signals it to do so. However, this enzyme does not exploit the reactive aldehyde group, but instead utilizes the phosphate group on PLP to perform its reaction.

Although the vast majority of PLP-dependent enzymes form an internal aldimine with PLP via an active site lysine residue; some PLP-dependent enzymes do not have this lysine residue, but instead have an active site histidine. In such a case, the histidine cannot form the internal aldimine, and, therefore, the cofactor never becomes covalently tethered to the enzyme. GDP-4-keto-6-deoxymannose-3-dehydratase (ColD) is an example of such an enzyme .

Biological Synthesis

It is synthesized from pyridoxal by the enzyme pyridoxal kinase, requiring one ATP. It is metabolized in the liver.

See also

• Aromatic-L-amino-acid decarboxylase
• Ornithine decarboxylase

References

1. Toney, M. D. "Reaction specificity in pyridoxal enzymes." Archives of biochemistry and biophysics (2005) 433: 279-287.
2. ^ Samuel, G. and Reeves, P. "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precusor synthesis and O-antigen assembly." Carbohydrate research (2003) 338:2503-2519.
3. Cook P. D., Thoden J.B. and Holden H. M. "The structure of GDP-4-keto-6-deoxymannose-3-dehydratase: a unique coenzyme B6-dependent enzyme." Protein Science (2006) 15:2093-2106.

External links

• A11HA06 (WHO)

• Articles with trivia sections from August 2009
• B vitamins