Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids

J Comb Chem. 2000 May-Jun;2(3):276-81. doi: 10.1021/cc990084b.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amines / chemistry
  • Carbodiimides / chemistry
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Guanidine / chemistry*

Substances

  • Amines
  • Carbodiimides
  • Carboxylic Acids
  • Guanidine