ArticleProceedings of the National Academy of Sciences of the United States of America2016
Nonenzymatic biomimetic remodeling of phospholipids in synthetic liposomes.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Breaking the membrane heredity paradox through de novo protocell formation.Nature communications · 2026Article
- Diacylation of Peptides Enables the Construction of Functional Vesicles for Drug-Carrying Liposomes.Angewandte Chemie (International ed. in English) · 2025Article
- Protocells by spontaneous reaction of cysteine with short-chain thioesters.Nature chemistry · 2025Article
- Functional metal-phenolic cortical cytoskeleton for artificial cells.Science advances · 2024Article
- Biomimetic construction of phospholipid membranes by direct aminolysis ligations.Interface focus · 2023Article
- Synthesis of lipid membranes for artificial cells.Nature reviews. Chemistry · 2021Review
- Dynamic spatial and structural organization in artificial cells regulates signal processing by protein scaffolding.Chemical science · 2020Article
- Lipids: chemical tools for their synthesis, modification, and analysis.Chemical Society reviews · 2020Review
- Traceless native chemical ligation of lipid-modified peptide surfactants by mixed micelle formation.Nature communications · 2020Article
- Twenty Years of "Lipid World": A Fertile Partnership with David Deamer.Life (Basel, Switzerland) · 2019Review
- Length-Selective Synthesis of Acylglycerol-Phosphates through Energy-Dissipative Cycling.Journal of the American Chemical Society · 2019Article
- Liquid-liquid phase separation in artificial cells.Interface focus · 2018Article
- Biomimetic Generation and Remodeling of Phospholipid Membranes by Dynamic Imine Chemistry.Journal of the American Chemical Society · 2018Article
- Biomimetic artificial organelles with in vitro and in vivo activity triggered by reduction in microenvironment.Nature communications · 2018Article
- Review
- Article
- Exploring chemoselective S-to-N acyl transfer reactions in synthesis and chemical biology.Nature communications · 2017Review
- Artificial Cells: Synthetic Compartments with Life-like Functionality and Adaptivity.Accounts of chemical research · 2017Review
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cell membranes have a vast repertoire of phospholipid species whose structures can be dynamically modified by enzymatic remodeling of acyl chains and polar head groups. Lipid remodeling plays important roles in membrane biology and dysregulation can lead to disease. Although there have been tremendous advances in creating artificial membranes to model the properties of native membranes, a major obstacle has been developing straightforward methods to mimic lipid membrane remodeling. Stable liposomes are typically kinetically trapped and are not prone to exchanging diacylphospholipids. Here, we show that reversible chemoselective reactions can be harnessed to achieve nonenzymatic spontaneous remodeling of phospholipids in synthetic membranes. Our approach relies on transthioesterification/acyl shift reactions that occur spontaneously and reversibly between tertiary amides and thioesters. We demonstrate exchange and remodeling of both lipid acyl chains and head groups. Using our synthetic model system we demonstrate the ability of spontaneous phospholipid remodeling to trigger changes in vesicle spatial organization, composition, and morphology as well as recruit proteins that can affect vesicle curvature. Membranes capable of chemically exchanging lipid fragments could be used to help further understand the specific roles of lipid structure remodeling in biological membranes.
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Registered trials
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