5′-Phosphoribosylformylglycinamidine Explained

5′-Phosphoribosylformylglycinamidine (or FGAM) is a biochemical intermediate in the formation of purine nucleotides via inosine-5-monophosphate, and hence is a building block for DNA and RNA.[1] [2] The vitamins thiamine[3] [4] and cobalamin[5] also contain fragments derived from FGAM.[6]

The compound is biosynthesized from phosphoribosyl-N-formylglycineamide (FGAR) which is converted to an amidine by the action of phosphoribosylformylglycinamidine synthase, transferring an amino group from glutamine in a reaction that also requires ATP:

FGAR + ATP + glutamine + H2O → FGAM + ADP + glutamate + PiThe biosynthesis pathway next converts FGAM to 5-aminoimidazole ribotide (AIR) by the action of AIR synthetase which uses ATP to activate the terminal carbonyl group to attack by the nitrogen atom at the anomeric center:

FGAM + ATP → AIR + ADP + Pi + H+

See also

Notes and References

  1. Web site: Pathway: 5-aminoimidazole ribonucleotide biosynthesis I . R. Caspi . MetaCyc Metabolic Pathway Database . 2009-01-13 . 2022-02-02 .
  2. Book: 10.1007/978-981-16-0723-3_19 . Nucleotide Biosynthesis and Regulation . Fundamentals of Bacterial Physiology and Metabolism . 2021 . Gupta . Rani . Gupta . Namita . 525–554 . 978-981-16-0722-6 . 234897784 .
  3. Web site: Pathway: superpathway of thiamine diphosphate biosynthesis I . R. Caspi . MetaCyc Metabolic Pathway Database . 2011-09-14 . 2022-02-01 .
  4. 10.1002/anie.201003419 . A "Radical Dance" in Thiamin Biosynthesis: Mechanistic Analysis of the Bacterial Hydroxymethylpyrimidine Phosphate Synthase . 2010 . Chatterjee . Abhishek . Hazra . Amrita B. . Abdelwahed . Sameh . Hilmey . David G. . Begley . Tadhg P. . Angewandte Chemie International Edition . 49 . 46 . 8653–8656 . 20886485 . 3147014 .
  5. Web site: Pathway: 5-hydroxybenzimidazole biosynthesis (anaerobic) . R. Caspi . MetaCyc Metabolic Pathway Database . 2019-09-23 . 2022-02-10 .
  6. 10.1021/jacs.5b03576 . Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis . 2015 . Mehta . Angad P. . Abdelwahed . Sameh H. . Fenwick . Michael K. . Hazra . Amrita B. . Taga . Michiko E. . Zhang . Yang . Ealick . Steven E. . Begley . Tadhg P. . Journal of the American Chemical Society . 137 . 33 . 10444–10447 . 26237670 . 4753784 .

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