Prebiotic synthesis of 2-deoxy-d-ribose from interstellar building blocks promoted by amino esters or amino nitriles

Abstract

COMMUNICATION

Evaluation of Amino Nitriles and an Amino Imidate as Organo­catalysts in Aldol Reactions

“…1 H NMR (400 MHz, CDCl 3 ):  = 6.85 (1 H, s), 5.40-6.10 (1 H, m), 4.35-4.15 (1 H, m), 3.55-3.25 (2 H, m), 2.40-1.80 (4 H, m), 1.45 (9 H, s). HRMS (ESI): m/z [M + Na] + calcd for C 10 H 18 N 2 O 3 Na: 237.1210; found: 237.1209.Spectroscopic data are in agreement with the literature 8.…”

“…N. Vagkidis et al NMR (400 MHz, CDCl 3 ):  = 121.1, 49.7, 32.8, 18.8, 17.5. HRMS (ESI): m/z [M + H] + calcd for C 5 H 11 N 2 : 99.0917; found: 99.0919.Spectroscopic data are identical to that reported in the literature 8.…”

“…NMR (400 MHz, DMSO-d 6 ):  = 155.5, 135.7, 128.8, 128.6, 128.4, 117.8, 67.9, 49.1, 31.9, 18.7, 18.0. HRMS (ESI): m/z [M + Na] + calcd for C 13 H 16 N 2 O 2 Na: 255.1104; found: 255.1105.Spectroscopic data are identical to that reported in the literature 8.…”

“…8 +25.0 (c 1.0 g cm-3 in DMF)}.IR (ATR):3374, 3315 (N-H), 3201, 3030, 2972, 2958, 2895, 2872 (C-H), 1681, 1654 (C=O), 1243 cm -1 (C-O). 1 H NMR (400 MHz, DMSO-d 6 ):  = 7.38-7.28 (6 H, m), 7.16 (1 H, d, J = 8.9 Hz), 7.03 (1 H, br s), 5.03 (2 H, s), 3.80 (1 H, dd, J = 8.9, 6.6 Hz), 1.99-1.28 (1 H, app oct, J = 6.6 Hz), 0.86 (3 H, d, J = 6.6 Hz), 0.83 (3 H, d, J = 6.6 Hz).…”

A Prebiotic Synthesis of Canonical Pyrimidine and Purine Ribonucleotides

“…Likewise, prebiotic routes to ribose involving borate minerals are proposed (Ricardo et al, 2004; Kim et al, 2011; Furukawa and Kakegawa, 2017). Also, the prebiotic synthesis of enantiomeric enriched carbohydrates (Breslow et al, 2013) and 2-deoxy ribose are reported (Steer et al, 2017).…”