Beyond L-Proline: Investigation into the Catalytic Properties of Other Natural Amino Acids in an Organocatalytic Warfarin Synthesis

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 synthesi...

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Main Authors: Anna I. Wurz, Arhemy Franco-Gonzalez, Naomi R. Benson, Hope L. Jankowski, Sierra N. Carr, Ketan Chamakura, Lizbeth Chirinos, Sydney P. Coll, Kayla F. Ivory, Trinity J. Lamb, Shaya LeBauer, Grace L. McPherson, Thanh Nguyen, Jeimy Nolasco Guevara, Lily N. Parsad, Phuong Pham, Emma G. Piner, Kaci Richardson, Abdelhadi Bendjellal, Chelsea McRae, Robert M. Hughes
Format: Article
Language:English
Published: MDPI AG 2025-04-01
Series:Chemistry
Subjects:
warfarin
organocatalysis
L-arginine
<span style="font-variant: small-caps">d</span>-arginine
enantioselective
Online Access:https://www.mdpi.com/2624-8549/7/2/59
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Summary: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 <span style="font-variant: small-caps;">d</span>-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.
ISSN:2624-8549

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