ArticleNature chemistry2021
Chiral lipid bilayers are enantioselectively permeable.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Stereoselective Phosphorylation of d-Ribose as a Driver of Life's Homochirality.Life (Basel, Switzerland) · 2026Article
- An increased throughput workflow to identify ion transport and membrane lysis agents for antimicrobial discovery.Chemical science · 2026Article
- A cationic single-chain bolalipid forms stable vesicles with distinct interfacial behavior.Biophysical journal · 2026Article
- A generalizable assay for intracellular accumulation to profile cytosolic drug delivery in mammalian cells.Communications chemistry · 2026Article
- Assembling Lipid Membrane Scaffolds on Microgel-Based Artificial Cells through Vesicle Fusion onto the Hydrogel Network.ACS nano · 2026Article
- A catalyst-free bioorthogonal reaction for malononitrile addition to azodicarboxylates.Nature communications · 2025Article
- Fabrication of cytotoxic mirror image nanopores.Nature communications · 2025Article
- Passive Membrane Transport Analysis of Drug Mixtures.Analytical chemistry · 2025Article
- Permeability selection of biologically relevant membranes matches the stereochemistry of life on Earth.PLoS biology · 2025Article
- Prebiotic Peptide Synthesis: How Did Longest Peptide Appear?Journal of molecular evolution · 2025Review
- Probing the Effects of Chirality on Self-Assembling Peptides: Hydrogel Formation, Degradation, Antigen Release, and Adjuvancy.Cellular and molecular bioengineering · 2024Article
- The astrochemical evolutionary traits of phospholipid membrane homochirality.Nature reviews. Chemistry · 2024Review
- One-step simultaneous liquid phase exfoliation-induced chirality in graphene and their chirality-mediated microRNA delivery.Materials advances · 2023Article
- The protometabolic nature of prebiotic chemistry.Chemical Society reviews · 2023Review
- The Transport of Charged Molecules across Three Lipid Membranes Investigated with Second Harmonic Generation.Molecules (Basel, Switzerland) · 2023Article
- Liposomal Permeation Assay for Droplet-Scale Pharmacokinetic Screening.Journal of medicinal chemistry · 2023Article
- Systematic comparison of unilamellar vesicles reveals that archaeal core lipid membranes are more permeable than bacterial membranes.PLoS biology · 2023Article
- Label-free quantification of passive membrane permeability of cyclic peptides across lipid bilayers: penetration speed of cyclosporin A across lipid bilayers.Chemical science · 2023Article
- Stereoselectivity of Interaction of Nonsteroidal Anti-Inflammatory Drug S-Ketoprofen with L/D-Tryptophan in Phospholipid Membranes.Membranes · 2022Article
- Toward synthetic life: Biomimetic synthetic cell communication.Current opinion in chemical biology · 2021Review
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
Homochiral membrane bilayers organize biological functions in all domains of life. The membrane's permeability-its key property-correlates with a molecule's lipophilicity, but the role of the membrane's rich and uniform stereochemistry as a permeability determinant is largely ignored in empirical and computational measurements. Here, we describe a new approach to measuring permeation using continuously generated microfluidic droplet interface bilayers (DIBs, generated at a rate of 480 per minute) and benchmark this system by monitoring fluorescent dye DIB permeation over time. Enantioselective permeation of alkyne-labelled amino acids (Ala, Val, Phe, Pro) and dipeptides through a chiral phospholipid bilayer was demonstrated using DIB transport measurements; the biological L enantiomers permeated faster than the D enantiomers (from 1.2-fold to 6-fold for Ala to Pro). Enantioselective permeation both poses a potentially unanticipated criterion for drug design and offers a kinetic mechanism for the abiotic emergence of homochirality via chiral transfer between sugars, amino acids and lipids.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.