Compound 2b
glyceraldehyde
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Dihydroxyacetone (2q; 9 mg, 0.1 mmol) was dissolved in sodium phosphate buffer (pH 7, 1M, 1 mL, H2O/D2O 9:1). The conversion of 2q to glyceraldehyde (2b) was monitored at room temperature by 1H NMR spectroscopy. Multiplet signals corresponding to 2b started to appear after 24 h, with no significant change after 120 h, glyceraldehyde (2b) was present in no more than 10% of the total composition (Supplementary Figure 3). 1H NMR (300 MHz, H2O/D2O 9:1) rac-glyceraldehyde (2b·H2O): δ 3.63–3.68 (m, 1H, (C2)–H), 3.52–3.56 (m, 2H, (C3)–H), 3.48–3.51 (m, 1H, (C3)–H);
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