Solution- and Solid-Phase Syntheses of Substituted Guanidinocarboxylic Acids

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Abstract
A library of guanidine-based compounds was produced to mimic the lead compound 1, which is a substance known to have intensely sweet-taste characteristics. Libraries of guanidinocarboxylic acids were therefore prepared via two synthetic methods. The solid-phase method involving trapping of solution-phase carbodiimides by supported amines was used to produce N,N‘-dialkyl derivatives (Scheme 1). The second solid-phase method, featuring supported carbodiimides and solution-phase amines (Scheme 2), was devised to prepare N,N‘-disubstituted and N,N‘,N‘-trisubstituted guanidinocarboxylic acids. A small collection of guanadinoacetic acid dimers and trimers was also prepared, but this time via a solution-phase coupling of carbodiimides to a polyamine linker.