349-34-8

Basic information

• Product Name: phosphoribosyl-N-formylglycineamide
• Synonyms: phosphoribosyl-N-formylglycineamide;VDXLUNDMVKSKHO-JDNPWWSISA-N
• CAS NO: 349-34-8
• Molecular Formula: C₈H₁₅N₂O₉P
• Molecular Weight: 314.19
• Mol File: 349-34-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.71g/cm³
• Refractive Index: 1.582
• CAS DataBase Reference: phosphoribosyl-N-formylglycineamide(CAS DataBase Reference)
• NIST Chemistry Reference: phosphoribosyl-N-formylglycineamide(349-34-8)
• EPA Substance Registry System: phosphoribosyl-N-formylglycineamide(349-34-8)

Safety Data

• Hazardous Substances Data: 349-34-8(Hazardous Substances Data)

Usage

Description

Phosphoribosyl-N-formylglycineamide (also known as Formylglycinamide Ribotide or FGAR) is an intermediate compound in the purine biosynthetic pathway, which is a series of biochemical reactions that result in the formation of purine nucleotides. FGAR plays a crucial role in the synthesis of Formylglycinamidine Ribonucleotide (FGAM), a subsequent compound in the pathway.

Uses

Used in Biochemical Research:
Phosphoribosyl-N-formylglycineamide is used as a research compound for studying the purine biosynthetic pathway and its role in various cellular processes. Understanding the function and regulation of this pathway can provide insights into the development of potential therapeutic strategies for diseases related to purine metabolism.
Used in Pharmaceutical Industry:
FGAR is used as a key intermediate in the synthesis of various purine-based drugs, which have applications in the treatment of gout, certain types of cancer, and other conditions that involve disruptions in purine metabolism.
Used in Enzyme Assays:
Phosphoribosyl-N-formylglycineamide is used as a substrate in enzyme assays to study the activity of enzymes involved in the purine biosynthetic pathway, such as phosphoribosylformylglycinamidine synthase, which catalyzes the conversion of FGAR to FGAM.

InChI:InChI=1/C8H15N2O9P/c11-3-9-1-5(12)10-8-7(14)6(13)4(19-8)2-18-20(15,16)17/h3-4,6-8,13-14H,1-2H2,(H,9,11)(H,10,12)(H2,15,16,17)/t4-,6-,7-,8-/m1/s1

Upstream product

• 34980-66-0 D-ribose 5-phosphate 

Relevant articles and documents

Mass spectrometric analysis of purine de novo biosynthesis intermediates

Purines are essential molecules for all forms of life. In addition to constituting a backbone of DNA and RNA, purines play roles in many metabolic pathways, such as energy utilization, regulation of enzyme activity, and cell signaling. The supply of purines is provided by two pathways: the salvage pathway and de novo synthesis. Although purine de novo synthesis (PDNS) activity varies during the cell cycle, this pathway represents an important source of purines, especially for rapidly dividing cells. A method for the detailed study of PDNS is lacking for analytical reasons (sensitivity) and because of the commercial unavailability of the compounds. The aim was to fully describe the mass spectrometric fragmentation behavior of newly synthesized PDNS-related metabolites and develop an analytical method. Except for four initial ribotide PDNS intermediates that preferentially lost water or phosphate or cleaved the forming base of the purine ring, all the other metabolites studied cleaved the gly-cosidic bond in the first fragmentation stage. Fragmentation was possible in the third to sixth stages. A liquid chromatography-high-resolution mass spectrometric method was developed and applied in the analysis of CRISPR-Cas9 genome-edited HeLa cells deficient in the individual enzymatic steps of PDNS and the salvage pathway. The identities of the newly synthesized intermediates of PDNS were confirmed by comparing the fragmentation patterns of the synthesized metabolites with those produced by cells (formed under pathological conditions of known and theoretically possible defects of PDNS). The use of stable isotope incorporation allowed the confirmation of fragmentation mechanisms and provided data for future fluxomic experiments. This method may find uses in the diagnosis of PDNS disorders, the investigation of purinosome formation, cancer research, enzyme inhibition studies, and other applications.