Extended Data Fig. 1: Reaction of alanyl-thiol with nucleosides.
From: Thioester-mediated RNA aminoacylation and peptidyl-RNA synthesis in water
a, 1H NMR spectra show the reaction of: (i) l-\({{\bf{1}}}_{{\bf{A}}{\bf{l}}{\bf{a}}}^{{\bf{e}}}\) (200 mM) and cytidine 16C (20 mM) at pH 6.5, which yields aminoacyl-cytidine \({{\bf{17}}}_{{\bf{A}}{\bf{l}}{\bf{a}}}^{{\bf{C}}}\) (25%) after 24 h; (ii) l-\({{\bf{1}}}_{{\bf{A}}{\bf{l}}{\bf{a}}}^{{\bf{e}}}\) (100 mM), 16C (20 mM) and 5′-mercapto-adenosine 15 (15 mM) at pH 6.5 after 24 h; and (iii) l-\({{\bf{1}}}_{{\bf{A}}{\bf{l}}{\bf{a}}}^{{\bf{e}}}\) (100 mM) and 15 (20 mM) at pH 6.5, in which 2′,3′-diol aminoacylation (54%) is observed after 24 h. b, Structure of non-canonical nucleosides (20, 22–25) and ribonucleotides (26–32). c, Alcohol-aminoacylation yield for specified nucleosides (20 mM) with l-\({{\bf{1}}}_{{\bf{A}}{\bf{l}}{\bf{a}}}^{{\bf{e}}}\) (200 mM) at room temperature and pH 6.5 after 24 h. See Fig. 2c for canonical RNA and DNA nucleosides. For more experimental details, see Supplementary Figs. 48–69 and Supplementary Table 6.
