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Solution- and solid-phase syntheses of substituted guanidinocarboxylic acids
J Chen1, M Pattarawarapan, A J Zhang
1Department of Chemistry, Box 30012, Texas A&M University, College Station, Texas 77842-3012, USA.
Journal of Combinatorial Chemistry
|May 29, 2000
Summary
Researchers synthesized guanidine-based compounds to replicate a lead compound with intense sweetness. Two solid-phase methods and one solution-phase method were employed to create various guanidinocarboxylic acid derivatives and oligomers.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- A lead compound (1) exhibits intense sweetness, prompting interest in its structural analogs.
- Guanidine-based compounds are explored for their potential taste-modulating properties.
Purpose of the Study:
- To synthesize a library of guanidine-based compounds mimicking the sweet taste of lead compound 1.
- To explore novel synthetic routes for guanidinocarboxylic acids and their oligomers.
Main Methods:
- Preparation of N,N'-dialkyl guanidinocarboxylic acids using solid-phase synthesis (trapping carbodiimides by supported amines).
- Synthesis of N,N'-disubstituted and N,N',N'-trisubstituted guanidinocarboxylic acids via a second solid-phase method (supported carbodiimides with solution-phase amines).
- Solution-phase synthesis of guanadinoacetic acid dimers and trimers using carbodiimide coupling to a polyamine linker.
Main Results:
- Successfully generated diverse libraries of guanidine-based compounds.
- Developed and optimized two distinct solid-phase synthetic strategies.
- Produced guanadinoacetic acid oligomers through solution-phase coupling.
Conclusions:
- The study established efficient synthetic pathways for creating guanidine-based compounds with potential applications in taste modification.
- The developed methods offer versatility in producing a range of substituted guanidinocarboxylic acids and oligomers.