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Chiral lipid bilayers are enantioselectively permeable
Juan Hu1, Wesley G Cochrane1, Alexander X Jones2
1Department of Pharmaceutical Sciences, University of California, Irvine, CA, USA.
Nature Chemistry
|June 11, 2021
Summary
Chiral phospholipid bilayers show enantioselective permeation, with L-amino acids crossing faster than D-amino acids. This finding impacts drug design and explains the origin of homochirality in biological systems.
Area of Science:
- Biochemistry
- Chemical Biology
- Origins of Life Research
Background:
- Homochiral membrane bilayers are fundamental to biological organization.
- Membrane permeability is linked to lipophilicity, but the role of stereochemistry is understudied.
- Understanding chiral interactions in membranes is crucial for biological and chemical processes.
Purpose of the Study:
- To develop and validate a novel microfluidic system for measuring membrane permeation.
- To investigate the enantioselective permeation of amino acids and dipeptides through chiral phospholipid bilayers.
- To explore the implications of enantioselective permeation for drug design and the origin of homochirality.
Main Methods:
- Utilized continuously generated microfluidic droplet interface bilayers (DIBs) at a high rate (480/min).
- Monitored the permeation of fluorescent dyes and alkyne-labeled amino acids/dipeptides over time.
- Quantified the transport rates of L- and D-enantiomers across chiral phospholipid bilayers.
Main Results:
- Demonstrated enantioselective permeation of amino acids (Ala, Val, Phe, Pro) and dipeptides through chiral DIBs.
- Observed faster permeation of biological L-enantiomers compared to D-enantiomers (1.2 to 6-fold difference).
- Validated the DIB system's capability for precise permeation measurements.
Conclusions:
- Enantioselective permeation is a significant factor in membrane transport, previously overlooked.
- This finding introduces a new criterion for chiral drug design and delivery.
- Enantioselective permeation provides a potential kinetic mechanism for the abiotic emergence of homochirality from simpler chiral molecules.
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