Synthesis and characterization of alanine-derived nucleoside analogues

Abstract

In this work, a series of new nucleoside analogues derived from alanine were synthesized using a multistep method involving Schiff base formation, Pictet–Spengler-type cyclization, glycosylation with protected fructose, and subsequent deacetylation. This synthetic approach enabled the construction of fused heterocyclic systems incorporating both amino acid and sugar moieties, resembling natural nucleoside structures. TLC, melting point analysis, FT-IR, and detailed 1H and 13C NMR spectroscopy were employed to characterize the key intermediates and final products. The inclusion of alanine introduced pharmacophoric functionality, facilitating ring closure and potentially enhancing biological selectivity. Additionally, the use of a per acetylated fructose derivative improved glycosylation efficiency and structural stability. The resulting deprotected compounds exhibited well-defined structures, rendering them suitable for future bioactivity screening. Overall, the proposed methodology offers a promising synthetic platform for the development of structurally diverse and biologically relevant nucleoside mimics.