5′-Phosphoribosylformylglycinamidine
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]
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Names | |
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IUPAC name [(2R,3S,4R,5R)-5-[(1-Amino-2-formamidoethylidene)amino]-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate | |
Other names FGAM | |
Identifiers | |
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Properties | |
C8H16N3O8P | |
Molar mass | 313.20 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
The compound is biosynthesized from phosphoribosyl-N-formylglycineamide (FGAR) which is converted to an amidine by the action of phosphoribosylformylglycinamidine synthase (EC 6.3.5.3), transferring an amino group from glutamine in a reaction that also requires ATP:
- FGAR + ATP + glutamine + H2O → FGAM + ADP + glutamate + Pi
The biosynthesis pathway next converts FGAM to 5-aminoimidazole ribotide (AIR) by the action of AIR synthetase (EC 6.3.3.1) which uses ATP to activate the terminal carbonyl group to attack by the nitrogen atom at the anomeric center: