ArticleChemical science2015
Rapid access to phospholipid analogs using thiol-yne chemistry.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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Who cites it
8 citing papers in PubMed, 23 citations in OpenAlex.
- Preparation, characterization and antioxidative activity analysis of recombinant humanized collagen type III-loaded liposomes.Scientific reports · 2025Article
- Article
- Cyanuric chloride as the basis for compositionally diverse lipids.RSC advances · 2021Article
- Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside.Beilstein journal of organic chemistry · 2019Article
- Review
- A bioinspired and biocompatible ortho-sulfiliminyl phenol synthesis.Nature communications · 2017Article
- Visible light mediated metal-free thiol-yne click reaction.Chemical science · 2016Article
- Towards self-assembled hybrid artificial cells: novel bottom-up approaches to functional synthetic membranes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Phospholipids and glycolipids constitute an essential part of biological membranes, and are of tremendous fundamental and practical interest. Unfortunately, the preparation of functional phospholipids, or synthetic analogs, is often synthetically challenging. Here we utilize thiol-yne click chemistry methodology to gain access to phospho- and glycolipid analogs. Alkynyl hydrophilic head groups readily photoreact with numerous thiol modified lipid tails to yield the appropriate dithioether phospho- or glycolipids. The resulting structures closely resemble the structure and function of native diacylglycerolipids. Dithioether phosphatidylcholines (PCs) are suitable for forming giant unilamellar vesicles (GUV), which can be used as vessels for cell-free expression systems. The unnatural thioether linkages render the lipids resistant to phospholipase A2 hydrolysis. We utilize the improved stability of these lipids to control the shrinkage of GUVs composed of a mixture of 1,2-dioleoyl-
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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.