Thiol-yne 'Click' Chemistry As a Route to Functional Lipid Mimetics
Polymers and High Performance Materials
Thiol-alkyne 'click' chemistry is a modular, efficient mechanism to synthesize complex A(2)B 3-arm star polymers. This general motif is similar to a phospholipid where the A blocks correspond to lypophilic chains and the B block represents the polar head group. In this communication we employ thiol-yne chemistry to produce polypeptide-based A2B lipid mimetics. The utility of the thiol-yne reaction is demonstrated by using a divergent and a convergent approach in the synthesis. These polymers self-assemble in aqueous solution into spherical vesicles with a relatively narrow size distribution independent of block composition over the range studied. Using the thiol-yne convergent synthesis, we envision a modular approach to functionalize proteins or oligopeptides with lipophilic chains that can imbed seamlessly into a cell membrane.
Naik, S. S.,
Chan, J. W.,
Hoyle, C. E.,
Savin, D. A.
(2011). Thiol-yne 'Click' Chemistry As a Route to Functional Lipid Mimetics. Polymer Chemistry, 2(2), 303-305.
Available at: http://aquila.usm.edu/fac_pubs/522