Beyond L-Proline: Investigation into the Catalytic Properties of Other Natural Amino Acids in an Organocatalytic Warfarin Synthesis
Proline is considered the model organocatalytic amino acid. However, other naturally occurring amino acids remain a potent and perhaps overlooked source of organocatalytic potential. In this work, we investigated the capacity of various natural amino acids to promote enantioselectivity in a synthesis of warfarin. We have identified L- and d-arginine as enantioselective catalysts for this reaction and have developed a recrystallization method to isolate the enantiomers of warfarin with high enantiopurity. In addition, we used methylated derivatives of arginine to provide insight into the reaction mechanism.
Authors
- Robert M. Hughes (ORCID: https://orcid.org/0000-0002-4465-4212)
- Phuong Pham (ORCID: https://orcid.org/0000-0002-8802-2188)
- Thanh Nguyen (ORCID: https://orcid.org/0000-0002-7246-634X)
- Anna I. Wurz (ORCID: https://orcid.org/0000-0003-0321-2888)
- Shaya LeBauer
- Lily Parsad
- Emma Piner
- Abdelhadi Bendjellal
- Chelsea McRae
- Ketan Chamakura (ORCID: https://orcid.org/0009-0009-0077-9812)
- Lizbeth Chirinos
- Arhemy Franco-Gonzalez
- Kayla Ivory
- Trinity Lamb
- Sierra Carr
- Jeimy Nolasco Guevara
- N Benson
- Kaci Richardson
- Sydney Coll (ORCID: https://orcid.org/0009-0000-8529-0980)
- Hope Jankowski
- Grace McPherson
Institutions
- East Carolina University (US)
Publication Details
- Journal
- Chemistry
- Published
- 2025-04-04
- DOI
- https://doi.org/10.3390/chemistry7020059
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Science Foundation