Thiol-yne 'Click' Chemistry As a Route to Functional Lipid Mimetics

Authors

Sandeep S. Naik, University of Southern Mississippi
Justin W. Chan, University of Southern Mississippi
Christopher Comer, University of Southern Mississippi
Charles E. Hoyle, University of Southern MississippiFollow
Daniel A. Savin, University of Southern MississippiFollow

Document Type

Article

Publication Date

2011

Department

Polymers and High Performance Materials

Abstract

Thiol-alkyne 'click' chemistry is a modular, efficient mechanism to synthesize complex A₂B 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.

Publication Title

Polymer Chemistry

Volume

2

Issue

2

First Page

303

Last Page

305

Recommended Citation

Naik, S. S., Chan, J. W., Comer, C., 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: https://aquila.usm.edu/fac_pubs/522