Beyond L-proline: Investigation of the properties of other natural amino acids in an organocatalytic warfarin synthesis
Year: 2025
Type: preprint
Abstract: 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 provide insight into the reaction mechanism.
Source: ChemRxiv
Authors: Anna Wurz, Naomi Benson, Arhemy Franco-Gonzalez, Hope Jankowski, Sierra Carr, Ketan Chamakura, Lizbeth Chirinos, Sydney Coll, Kayla Ivory, Trinity Lamb, Shaya LeBauer, Grace McPherson, Thanh Nguyen, Jeimy Nolasco Guevara, Lily Parsad, Phuong Pham, Emma Piner, Kaci Richardson, Abdelhadi Bendjellal, Chelsea McRae, Robert Hughes
Institution: East Carolina University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4408883428