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Phosphoribosyl pyrophosphate

PRPP Phosphoribosyl pyrophosphate (PRPP) is a pentose phosphate. It is a biochemical intermediate in the formation of purine nucleotides via inosine-5-monophosphate, as well as in pyrimidine nucleotide formation. Hence it is a building block for DNA and RNA. The vitamins thiamine and cobalamin, and the amino acid tryptophan also contain fragments derived from PRPP. It is formed from ribose 5-phosphate (R5P) by the enzyme ribose-phosphate diphosphokinase: :[[File:R5pactivation.png|500px]]

It plays a role in transferring phospho-ribose groups in several reactions, some of which are salvage pathways:

EnzymeReactantProduct
adenine phosphoribosyltransferaseadenineAMP
hypoxanthine-guanine phosphoribosyltransferaseguanineGMP
hypoxanthine-guanine phosphoribosyltransferasehypoxanthineIMP
nicotinate phosphoribosyltransferasenicotinatenicotinate riboside
orotate phosphoribosyltransferaseorotateOMP
uracil phosphoribosyltransferaseuracilUMP
xanthine phosphoribosyltransferasexanthineXMP

In de novo generation of purines, the enzyme amidophosphoribosyltransferase acts upon PRPP to create phosphoribosylamine. The same is true for the biosynthesis of tryptophan, with the first step being N-alkylation of anthranilic acid catalysed by the enzyme anthranilate phosphoribosyltransferase.

Increased PRPP

Increased levels of PRPP are characterized by the overproduction and accumulation of uric acid leading to hyperuricemia and hyperuricosuria. It is one of the causes of gout.

Increased levels of PRPP are present in Lesch–Nyhan Syndrome. Decreased levels of hypoxanthine guanine phosphoribosyl transferase (HGPRT) causes this accumulation, as PRPP is a substrate used by HGPRT during purine salvage.

References

References

  1. Ron Caspi. (2009-01-13). "Pathway: 5-aminoimidazole ribonucleotide biosynthesis I". MetaCyc Metabolic Pathway Database.
  2. (2008). "Structural biology of the purine biosynthetic pathway". Cellular and Molecular Life Sciences.
  3. (2021). "Fundamentals of Bacterial Physiology and Metabolism".
  4. (2010). "A "Radical Dance" in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase". Angewandte Chemie International Edition.
  5. Ron Caspi. (2019-09-23). "Pathway: 5-hydroxybenzimidazole biosynthesis (anaerobic)". MetaCyc Metabolic Pathway Database.
  6. (2015). "Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis". Journal of the American Chemical Society.
  7. (January 2007). "Crystal structure of human phosphoribosylpyrophosphate synthetase 1 reveals a novel allosteric site". Biochemical Journal.
  8. Ron Caspi. (2022-02-15). "5-phospho-α-D-ribose 1-diphosphate". MetaCyc Metabolic Pathway Database.
  9. (2008). "Structural Complexes of Human Adenine Phosphoribosyltransferase Reveal Novel Features of the APRT Catalytic Mechanism". Journal of Biomolecular Structure and Dynamics.
  10. (2002). "Mutational spectral analysis at the HPRT locus in healthy children". Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis.
  11. (1993). "A new paradigm for biochemical energy coupling. Salmonella typhimurium nicotinate phosphoribosyltransferase". Journal of Biological Chemistry.
  12. (2007). "Ternary Complex Formation and Induced Asymmetry in Orotate Phosphoribosyltransferase". Biochemistry.
  13. (2012). "Dynamic dissociating homo-oligomers and the control of protein function". Archives of Biochemistry and Biophysics.
  14. (1970). "Guanine and Xanthine Phosphoribosyltransfer Activities of Lactobacillus casei and Escherichia coli". Journal of Biological Chemistry.
  15. Voet, Donald. (2016). "Fundamentals of biochemistry : life at the molecular level".
  16. Ron Caspi. (2008-10-10). "Pathway: L-histidine biosynthesis". MetaCyc Metabolic Pathway Database.
  17. (2006). "Histidine biosynthesis in plants". Amino Acids.
  18. C.A. Fulcher. (2010-02-12). "Pathway: L-tryptophan biosynthesis". MetaCyc Metabolic Pathway Database.
  19. (1989). "Evolution of a Biosynthetic Pathway: The Tryptophan Paradigm". Annual Review of Microbiology.
  20. (16 September 2009). "Purine and Pyrimidine Metabolism". John Wiley & Sons.
  21. (2019). "Macrocytic anemia in Lesch–Nyhan disease and its variants". Genetics in Medicine.
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organophosphates monosaccharides
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