8318. SAICAR

Nomenclature

CAS number: 3031-95-6
N-[[5-Amino-1-(5-O-phosphono-β-d-ribofuranosyl)-1H-imidazol-4-yl]carbonyl]-l-aspartic acid; N-[(5-amino-1-ribofuranosylimidazol-4-yl)carbonyl]aspartic acid 5′-phosphate; 5-amino-N-(1,2-dicarboxyethyl)-1-ribofuranosylimidazole-4-carboxamide 5′-phosphate; 5-amino-4-imidazole-N-succinocarboxamide ribonucleotide; 5-amino-4-imidazole-N-succinocarboxamide ribotide; N-[5-amino-1-(5′-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid; succino-AICAR.
C13H19N4O12P; mol wt 454.28.
C 34.37%, H 4.22%, N 12.33%, O 42.26%, P 6.82%.

Description and references

Important purine precursor. Synthesis by enzymic reaction according to the equation AIR + ATP + aspartic acid + CO2 → SAICAR + ADP + orthophosphate: Lukens, Buchanan, J. Biol. Chem. 234, 1791 (1959). Production by adenine-requiring mutants of Bacillus subtilis: Ohmura et al., US 3280007 (1966 to Takeda). Synthesis of SAICAR and derivatives: Burrows, Shaw, J. Chem. Soc. C 1967, 1088; Burrows et al., ibid. 1968, 40.

Chemical structure

Derivative

Dibarium salt.
C13H15Ba2N4O12P; mol wt 724.91.
C 21.54%, H 2.09%, Ba 37.89%, N 7.73%, O 26.49%, P 4.27%.

Properties

uv max (pH 1): 269, 244 nm (ε 11850, 9580). If the Bratton-Marshall procedure [J. Biol. Chem. 128, 537 (1939)] is modified by keeping the sample in ice during, and for 10 minutes after the addition of the reagents, SAICAR produces a purple chromophore having max absorption at 550 nm. The diazonium salt of SAICAR is very unstable and dec before it can couple under the usual test conditions.