Catalytic Synthesis of Riboside–Amino Acid Hybrids

Abstract

The catalytic synthesis of 3-(2′-glycinoyl)ribose derivatives under mild conditions is described. The key reaction involves silver-catalyzed condensation of isocyanoacetates with 3-ketoriboses.

Key words

catalytic - non-coded amino acids - hybrid peptides - ­ribonucleoproteins - asymmetric synthesis

• References and Notes


See, for instance:
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For reports of nucleophilic additions to 3-ketonucleosides, see:
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• 5 Stereochemistry tentatively assigned by analogy with reported nucleophilic addition reactions of 3-ketoriboses.
• 6 3a: ¹H NMR (250 MHz, CDCl₃): δ = 2.00 (dd, J = 4.7, 14.5 Hz, 1 H), 2.37 (dd, J = 5.0, 14.5 Hz, 1 H), 3.18 (dd, J = 7.3, 10.0 Hz, 1 H), 3.30 (s, 1 H), 3.54 (dd, J = 5.2, 10.0 Hz, 1 H), 3.79 (s, 6 H), 3.80 (s, 3 H), 4.19 (dd, J = 5.2, 7.3 Hz, 1 H), 4.96 (d, J = 2.5 Hz, 1 H), 5.07 (dd, J = 4.7, 5.0 Hz, 1 H), 6.74 (d, J = 2.5 Hz, 1 H), 6.80–6.85 (m, 4 H), 7.15–7.41 (m, 8 H). ¹³C NMR (62.5 MHz, CDCl₃): δ = 43.0, 52.6, 55.2, 55.8, 60.9, 70.8, 81.4, 87.0, 92.0, 103.8, 113.0–144.3, 155.8, 158.5, 169.9.
• 7 4a: ¹H NMR (250 MHz, CDCl₃): δ = 2.00 (dd, J = 4.7, 14.5 Hz, 1 H), 2.37 (dd, J = 5.0, 14.5 Hz, 1 H), 3.18 (dd, J = 7.3, 10.0 Hz, 1 H), 3.30 (s, 1 H), 3.54 (dd, J = 5.2, 10.0 Hz, 1 H), 3.79 (s, 6 H), 3.80 (s, 3 H), 4.19 (dd, J = 5.2, 7.3 Hz, 1 H), 4.96 (d, J = 2.5 Hz, 1 H), 5.07 (dd, J = 4.7, 5.0 Hz, 1 H), 6.74 (d, J = 2.5 Hz, 1 H), 6.80–6.85 (m, 4 H), 7.15–7.41 (m, 8 H). ¹³C NMR (62.5 MHz, CDCl₃): δ = 45.4, 52.6, 53.5, 55.1, 56.7, 64.4, 80.6, 84.6, 86.9, 104.3, 113.2–158.6, 160.8, 169.3.