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Merck

P9255

Sigma-Aldrich

Pyridoxal 5′-phosphate hydrate

≥98%

Sinónimos:

Pyridoxal phosphate, 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde, Codecarboxylase, PLP, Pyridoxal 5-phosphate

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About This Item

Fórmula empírica (notación de Hill):
C8H10NO6P · xH2O
Número de CAS:
Peso molecular:
247.14 (anhydrous basis)
Beilstein/REAXYS Number:
234749
EC Number:
MDL number:
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.79
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biological source

synthetic (organic)

Quality Level

assay

≥98%

form

powder

technique(s)

HPLC: suitable

color

beige
off-white to yellow

mp

140-143 °C

storage temp.

−20°C

SMILES string

CC1=NC=C(COP(O)(O)=O)C(C([H])=O)=C1O

InChI

1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)

InChI key

NGVDGCNFYWLIFO-UHFFFAOYSA-N

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General description

Pyridoxal 5′-phosphate (PLP) is synthesized in a multiple-step process. The two pathways inlcude pyridoxal phosphate biosynthetic protein (PdxA)- pyridoxine-5′-phosphate synthase (PdxJ) pathway and the pyridoxal 5′-phosphate synthase subunit PDX1/PDX2 pathway.[1] It is the active form of pyridoxine.[2]

Application

Pyridoxal 5′-phosphate hydrate has also been used:
  • as a reference standard to quantify vitamin B6 in feed and digesta samples using high performance liquid chromatography (HPLC)[3]
  • in D-amino acid transaminase reaction(10)
  • as a cofactor for L-glutamic acid decarboxylase[4]

Biochem/physiol Actions

Pyridoxal 5′-phosphate (PLP) aids in carbohydrate and fat metabolism by serving as a cofactor. It is majorly responsible for catalyzing the enzymatic reactions involved in sphingolipid synthesis and neurotransmitter (dopamine and serotonin) synthesis.[2] PLP is used in the studies of PLP-dependent enzyme active sites. PLP is also a cofactor for a wide range of enzymes including mitochondrial 5-Aminolevulinic acid synthase (ALAS)[5] cysteine desulfurase,[6] cystathionine γ-synthase (CGS),[7] ornithine 4,5-aminomutase (OAM),[8] and D-serine dehydratase.[9]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Visite la Librería de documentos

Structure of the mitochondrial aminolevulinic acid synthase, a key heme biosynthetic enzyme
Brown BL, et al.
Structure, 26(4), 580-589 (2018)
Functional characterization of the eukaryotic cysteine desulfurase Nfs1p from Saccharomyces cerevisiae
Muhlenhoff U, et al.
Test, 279(35), 36906-36915 (2004)
A catalytic mechanism that explains a low catalytic activity of serine dehydratase like-1 from human cancer cells: crystal structure and site-directed mutagenesis studies
Yamada T, et al.
Biochim. Biophys. Acta Gen. Subj., 1780(5), 809-818 (2008)
Physical and enzymological interaction of Bacillus subtilis proteins required for de novo pyridoxal 5?-phosphate biosynthesis
Belitsky BR
Journal of Bacteriology, 186(4), 1191-1196 (2004)
Structure of the cystathionine gamma-synthase MetB from Mycobacterium ulcerans
Clifton MC, et al.
Acta Crystallographica. Section F, Structural Biology Communications, 67(9), 1154-1158 (2011)

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Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

Questions

1–2 of 2 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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