Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids.
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.
Chen
J
J
Department of Chemistry, Box 30012, Texas A&M University, College Station, Texas 77842-3012, USA.
Pattarawarapan
M
M
Zhang
A J
AJ
Burgess
K
K
D000588:Amines / Q000737:chemistry; D002234:Carbodiimides / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry*
D000588:Amines; D002234:Carbodiimides; D002264:Carboxylic Acids; D019791:Guanidine