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Phosphoribosylamine

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(Redirected from 5'-phosphoribosylamine)
Phosphoribosylamine
Names
Other names PRA
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH Phosphoribosylamine
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H12NO7P/c6-5-4(8)3(7)2(13-5)1-12-14(9,10)11/h2-5,7-8H,1,6H2,(H2,9,10,11)/t2-,3-,4-,5?/m1/s1Key: SKCBPEVYGOQGJN-SOOFDHNKSA-N
SMILES
  • C(1((C(O1)N)O)O)OP(=O)(O)O
Properties
Chemical formula C5H12NO7P
Molar mass 229.125 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Phosphoribosylamine (PRA) is a biochemical intermediate in the formation of purine nucleotides via inosine-5-monophosphate, and hence is a building block for DNA and RNA. The vitamins thiamine and cobalamin also contain fragments derived from PRA.

Phosphoribosyl pyrophosphate (PRPP)

It is the product of the enzyme amidophosphoribosyltransferase which attaches ammonia from glutamine to phosphoribosyl pyrophosphate (PRPP) at its anomeric carbon:

PRPP + glutamine → PRA + glutamate + PPi

The biosynthesis pathway next combines PRA with glycine in a process driven by ATP giving glycineamide ribonucleotide (GAR). The enzyme phosphoribosylamine—glycine ligase catalyses the reaction forming an amide bond:

PRA + glycine + ATP → GAR + ADP + Pi

See also

References

  1. R. Caspi (2009-01-13). "Pathway: 5-aminoimidazole ribonucleotide biosynthesis I". MetaCyc Metabolic Pathway Database. Retrieved 2022-02-02.
  2. ^ Zhang, Y.; Morar, M.; Ealick, S.E. (2008). "Structural biology of the purine biosynthetic pathway". Cellular and Molecular Life Sciences. 65: 3699–3724. doi:10.1007/s00018-008-8295-8. PMC 2596281. PMID 18712276.
  3. Gupta, Rani; Gupta, Namita (2021). "Nucleotide Biosynthesis and Regulation". Fundamentals of Bacterial Physiology and Metabolism. pp. 525–554. doi:10.1007/978-981-16-0723-3_19. ISBN 978-981-16-0722-6. S2CID 234897784.
  4. Chatterjee, Abhishek; Hazra, Amrita B.; Abdelwahed, Sameh; Hilmey, David G.; Begley, Tadhg P. (2010). "A "Radical Dance" in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase". Angewandte Chemie International Edition. 49 (46): 8653–8656. doi:10.1002/anie.201003419. PMC 3147014. PMID 20886485.
  5. R. Caspi (2019-09-23). "Pathway: 5-hydroxybenzimidazole biosynthesis (anaerobic)". MetaCyc Metabolic Pathway Database. Retrieved 2022-02-10.
  6. Mehta, Angad P.; Abdelwahed, Sameh H.; Fenwick, Michael K.; Hazra, Amrita B.; Taga, Michiko E.; Zhang, Yang; Ealick, Steven E.; Begley, Tadhg P. (2015). "Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis". Journal of the American Chemical Society. 137 (33): 10444–10447. doi:10.1021/jacs.5b03576. PMC 4753784. PMID 26237670.
  7. Welin, Martin; Grossmann, Jörg Günter; Flodin, Susanne; Nyman, Tomas; Stenmark, Pål; Trésaugues, Lionel; Kotenyova, Tetyana; Johansson, Ida; Nordlund, Pär; Lehtiö, Lari (2010). "Structural studies of tri-functional human GART". Nucleic Acids Research. 38 (20): 7308–7319. doi:10.1093/nar/gkq595. PMC 2978367. PMID 20631005.
Nucleotide metabolic intermediates
purine
metabolism
anabolism
R5P→IMP:
IMP→AMP:Adenylosuccinate
IMP→GMP:Xanthosine monophosphate
catabolism
pyrimidine
metabolism
anabolism
catabolism
uracil:
thymine:
Categories: