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P8296

Sigma-Aldrich

5-Phospho-D-ribose 1-diphosphate pentasodium salt

≥75% (HPLC)

Synonym(s):

α-D-Ribosyl diphosphate 5-phosphate pentasodium salt, 5-Phospho-α-D-ribosyl diphosphate, 5-Phosphoribosyl 1-pyrophosphate pentasodium salt, P-Rib-PP, PRPP pentasodium salt

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About This Item

Empirical Formula (Hill Notation):
C5H8Na5O14P3
CAS Number:
108321-05-7
Molecular Weight:
499.98
Beilstein:
6043637
MDL number:
MFCD32182529
UNSPSC Code:
12352201
PubChem Substance ID:
24898743
NACRES:
NA.25

Assay

≥75% (HPLC)

form

powder

impurities

<18% water (Karl Fischer)

color

white

solubility

water: 50 mg/mL, clear to slightly hazy, colorless to very faintly yellow

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Na+].[Na+].[Na+].[Na+].O[C@H]1[C@@H](O)[C@H](O[C@@H]1COP(O)([O-])=O)OP([O-])(=O)OP([O-])([O-])=O

InChI

1S/C5H13O14P3.4Na/c6-3-2(1-16-20(8,9)10)17-5(4(3)7)18-22(14,15)19-21(11,12)13;;;;/h2-7H,1H2,(H,14,15)(H2,8,9,10)(H2,11,12,13);;;;/q;4*+1/p-4/t2-,3-,4-,5?;;;;/m1..../s1

InChI key

QZAPPJHVNYCTAX-CKJQBBATSA-J

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Application

Pentasodium salt has been used in a study to assess the relationship between the muscarinic receptor cationic current and internal calcium in guinea-pig jejunal smooth muscle cells. It has also been used in a study to investigate inhibitors of the bacterial cell wall biosynthesis of the enzyme Mur D.

Substrates

Substrate for phosphoribosyltransferases in the synthesis of nucleotides.

Analysis Note

Purity ≥ 75% based on an assay system using orotidine-5′-phosphate pyrophosphorylase and orotidine-5′-phosphate decarboxylase mixed enzymes.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H371

Precautionary Statements

P260

Hazard Classifications

STOT SE 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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L D Gegnas et al.
Bioorganic & medicinal chemistry letters, 8(13), 1643-1648 (1999-01-05)
A series of transition-state analog inhibitors of the D-glutamic acid-adding enzyme (MurD) of bacterial peptidoglycan biosynthesis has been synthesized and evaluated for inhibition of the E. coli enzyme.
P Pacaud et al.
The Journal of physiology, 441, 477-499 (1991-09-01)
1. The action of carbachol, which activates muscarinic receptors, was studied in single patch-clamped cells where free internal calcium concentration in the cell (Cai2+) was estimated using the emission from the dye Indo-1. Cells were dialysed with potassium-free caesium solution
Nisreen Wahwah et al.
Scientific reports, 10(1), 19907-19907 (2020-11-18)
Cisplatin is a mainstay of cancer chemotherapy. It forms DNA adducts, thereby activating poly(ADP-ribose) polymerases (PARPs) to initiate DNA repair. The PARP substrate NAD+ is synthesized from 5-phosphoribose-1-pyrophosphate (PRPP), and we found that treating cells for 6 h with cisplatin reduced
Matthew Bratkowski et al.
Cell reports, 32(5), 107999-107999 (2020-08-07)
The NADase SARM1 is a central switch in injury-activated axon degeneration, an early hallmark of many neurological diseases. Here, we present cryo-electron microscopy (cryo-EM) structures of autoinhibited (3.3 Å) and active SARM1 (6.8 Å) and provide mechanistic insight into the tight regulation
Boyuan Wang et al.
Molecular cell, 80(1), 29-42 (2020-08-29)
(p)ppGpp is a nucleotide messenger universally produced in bacteria following nutrient starvation. In E. coli, ppGpp inhibits purine nucleotide synthesis by targeting several different enzymes, but the physiological significance of their inhibition is unknown. Here, we report the structural basis of

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