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. 2020 Jun 2;117(24):13267–13274. doi: 10.1073/pnas.1922139117

Table 1.

Concentrations, synthetic yields (%), and radiolytic yields (G) of the compounds relevant to 2-aminooxazole and 2-aminoimidazole synthesis

Compound Concentration, mM Yield,* % G
Cyanamide 0.65 2.6 0.13
Glyceronitrile 0.10 1.2 2.0•10−2
Cyanamide 2.8 1.1 5.7•10−2
Glyceronitrile 0.57 0.68 1.1•10−2
Glycolaldehyde 0.16 0.13 3.3•10−3
2-Aminooxazole§ 9.0•10−2 0.11 1.8•10−3
2-Aminoimidazole§ 5.5•10−2 6.6•10−2 1.1•10−3

All values were determined by 1H NMR integration against an internal standard of DMSO, except for the case of cyanamide, which was quantified by HPLC analysis after derivatization with dansyl chloride.

*

The yields are based on the initial amount of NaCN.

Concentrations measured in the irradiated sample before dry-down (SI Appendix, Fig. S17).

Concentrations measured after dry-down resulting in a ∼10-fold decrease in volume (SI Appendix, Fig. S18).

§

Concentrations measured after heating the sample following dry-down for 3 h at 50 °C (SI Appendix, Fig. S19).

The average concentration of 2-aminooxazole determined from two separate experiments.