Department
Chemistry
Advisor
James Christenson
Location
Bethel University
Document Type
Poster
Version
Preprint
Abstract
Beta-lactone synthetases are a class of enzymes which produce chiral beta-lactones, four-membered cyclic esters, from racemic beta-hydroxy acid substrates. Chiral beta-lactones are used as chemical synthons and as bioactive compounds, such as the FDA-approved drug, Orlistat. However, substrate specificity of stand-alone beta-lactone synthetases are poorly understood, and their use in chemoenzymatic synthesis of chiral bioactive compounds remains unexplored. This research focused on the organic synthesis of beta-hydroxy acids to probe the substrate specificity of this class of enzymes and to generate potentially bioactive compounds against essential tuberculosis enzymes. The beta-hydroxy acid 2-[(5-chlorofuran-2-yl)(hydroxy) methyl]hexanoic acid was synthesized from lithiated hexanoate and 5-chloro-2-furaldehyde under nitrogen gas, purified via liquid-liquid extraction, then characterized via 1H and 13C NMR.
Recommended Citation
Underwood, Laura Charlotte and Christenson, James, "Synthesis of disubstituted β-hydroxy acids for the enzymatic synthesis of chiral β-lactones" (2024). Science Symposium. 2.
https://spark.bethel.edu/science_symposium/spring2024/schedule2024/2
Terms of Use and License Information
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
Synthesis of disubstituted β-hydroxy acids for the enzymatic synthesis of chiral β-lactones
Bethel University
Beta-lactone synthetases are a class of enzymes which produce chiral beta-lactones, four-membered cyclic esters, from racemic beta-hydroxy acid substrates. Chiral beta-lactones are used as chemical synthons and as bioactive compounds, such as the FDA-approved drug, Orlistat. However, substrate specificity of stand-alone beta-lactone synthetases are poorly understood, and their use in chemoenzymatic synthesis of chiral bioactive compounds remains unexplored. This research focused on the organic synthesis of beta-hydroxy acids to probe the substrate specificity of this class of enzymes and to generate potentially bioactive compounds against essential tuberculosis enzymes. The beta-hydroxy acid 2-[(5-chlorofuran-2-yl)(hydroxy) methyl]hexanoic acid was synthesized from lithiated hexanoate and 5-chloro-2-furaldehyde under nitrogen gas, purified via liquid-liquid extraction, then characterized via 1H and 13C NMR.
Comments
beta-lactone, organic synthesis, antibiotics