Glycineamide ribonucleotide

Glycineamide ribonucleotide (or GAR) is an intermediate in de novo purine biosynthesis.

Glycineamide ribonucleotide

Names
IUPAC name [(2R,3S,4R,5R)-5-[(2-Aminoacetyl)amino]-3,4-dihydroxyoxolan-2-yl]methyldihydrogen phosphate
Other names Glycineamide ribotide, GAR
Identifiers
CAS Number	10074-18-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:143019
ChemSpider	141370
MeSH	Glycineamide+ribonucleotide
PubChem CID	160913
CompTox Dashboard (EPA)	DTXSID70143478
InChI InChI=1S/C7H15N2O8P/c8-1-4(10)9-7-6(12)5(11)3(17-7)2-16-18(13,14)15/h3,5-7,11-12H,1-2,8H2,(H,9,10)(H2,13,14,15)/t3-,5-,6-,7-/m1/s1 Key: OBQMLSFOUZUIOB-SHUUEZRQSA-N
SMILES C([C@@H]1[C@H]([C@H]([C@@H](O1)NC(=O)CN)O)O)OP(=O)(O)O
Properties
Chemical formula	C7H15N2O8P
Molar mass	286.177 g·mol^−1
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

It is formed from phosphoribosylamine by the enzyme phosphoribosylamine—glycine ligase. In the next step of purine biosynthesis the enzyme phosphoribosylglycinamide formyltransferase acts on GAR to form phosphoribosyl-N-formylglycineamide (FGAR).

GAR formation is stimulated by luteinizing hormone (LH) and chorionic gonadotropin (HCG) via activation of Glc-6-P-dehydrogenase (EC 1.1.1.49)[1][2]

Synonyms

Several names are associated with GAR:

• 5'-p-Ribosylglycinamide
• 5'-p-Ribosylglycineamide
• 5'-Phosphoribosyl-glycineamide
• 5'-Phosphoribosylglycinamide
• 5'-Phosphoribosylglycineamide
• Glycineamide ribotide
• Glycinamide ribonucleotide
• Glycineamide ribonucleotide
• N(1)-(5-Phospho-D-ribosyl)glycinamide
• N-Glycyl-5-O-phosphono-D-ribofuranosylamine
• N1-(5-phospho-D-ribosyl)glycinamide

References

1. "SMPDB: Glycineamideribotide". August 24, 2015.
2. "Human Metabolome Database: Glycineamideribotide". August 24, 2015.