Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids. Academic Article

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.

authors

• Burgess, Kevin

published proceedings

• J Comb Chem

altmetric score

• 3

author list (cited authors)

• Chen, J., Pattarawarapan, M., Zhang, A. J., & Burgess, K.

citation count

• 38

complete list of authors

• Chen, J||Pattarawarapan, M||Zhang, AJ||Burgess, K

publication date

• May 2000

publisher

• American Chemical Society (ACS)  Publisher

published in

• ACS Combinatorial Science  Journal

keywords

• Amines
• Carbodiimides
• Carboxylic Acids
• Guanidine

PubMed Central ID

• 10827936

Digital Object Identifier (DOI)

• 10.1021/cc990084b

start page

• 276

end page

• 281

volume

• 2

issue

• 3

URL

• http://dx.doi.org/10.1021/cc990084b