Glycineamide ribonucleotide

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Glycineamide ribonucleotide
Names
IUPAC name
(1R)-1,4-Anhydro-1-glycinamido-D-ribitol 5-(dihydrogen phosphate)
Systematic IUPAC name
[(2R,3S,4R,5R)-5-(2-Aminoacetamido)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
Glycineamide ribotide,
GAR
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
KEGG
UNII
  • 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 checkY
    Key: OBQMLSFOUZUIOB-SHUUEZRQSA-N checkY
  • C([C@@H]1[C@H]([C@H]([C@@H](O1)NC(=O)CN)O)O)OP(=O)(O)O
Properties
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).

Glycineamide ribonucleotide (or GAR) is a biochemical intermediate in the formation of

cobalamin[5] also contain fragments derived from GAR.[6]

Phosphoribosylamine (PRA)

GAR is the product of the enzyme phosphoribosylamine—glycine ligase acting on phosphoribosylamine (PRA) to combine it with glycine in a process driven by ATP. The reaction, EC 6.3.4.13 forms an amide bond:[7]

PRA + glycine + ATP → GAR + ADP + Pi

The biosynthesis pathway next adds a

10-formyltetrahydrofolate to GAR, catalysed by phosphoribosylglycinamide formyltransferase in reaction EC 2.1.2.2 and producing formylglycinamide ribotide (FGAR):[7]

GAR + 10-formyltetrahydrofolate → FGAR + tetrahydrofolate

See also

References

  1. ^ R. Caspi (2009-01-13). "Pathway: 5-aminoimidazole ribonucleotide biosynthesis I". MetaCyc Metabolic Pathway Database. Retrieved 2022-02-02.
  2. PMID 18712276
    .
  3. S2CID 234897784
    .
  4. PMID 20886485
    .
  5. ^ R. Caspi (2019-09-23). "Pathway: 5-hydroxybenzimidazole biosynthesis (anaerobic)". MetaCyc Metabolic Pathway Database. Retrieved 2022-02-10.
  6. PMID 26237670
    .
  7. ^
    PMID 20631005
    .
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