Metathesis polymerization of natural glycolipids

POLY 713

Sabine R. Wallner, swallner@poly.edu1, Wei Gao, wgao@poly.edu1, Rena Hagver1, Vishal Shah, vishand@hotmail.com1, Wenchun Xie, wen4192001@yahoo.com1, Harald Mang1, M. Firat Ilker2, Christen M. Bell2, Kelly A. Burke2, E. Bryan Coughlin, coughlin@mail.pse.umass.edu2, and Richard A. Gross, rgross@poly.edu1. (1) NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules, Department of Chemical and Biological Sciences, Polytechnic University, 6 Metrotech Center, Brooklyn, NY 11201, (2) Department of Polymer Science and Engineering, University of Massachusetts Amherst, 120 Governors Drive, Amherst, MA 01003
Polymers with amphiphilic properties are important components for a wide range of industrial and pharmaceutical products. Sophorolipids (SLs), extracellular surface-active glycolipids, show these properties as monomer building blocks. They are fermentatively produced in high yields by yeasts such as Candida bombicola when grown on sugars, hydrocarbons, vegetable oils or mixtures thereof. SLs consist of a carbohydrate (sophorose) polar head group and an unsaturated fatty acid moiety that is synthesized as a mixture of macrolactone and free acid structures. The predominant component of this mixture is the macrolactone fraction, which was used herein as a monomer for ruthenium-based Grubbs catalyzed ring-opening metathesis polymerizations (ROMP). The result was synthesis of poly(sophorolipids), a new functional polymer derived from this natural glycolipid precursor. Surprisingly, polymerization of this 26-membered ring glycolipid monomer proceeded efficiently yielding high molecular weight polymers.

Biocatalysis in Polymer Science
1:30 PM-4:45 PM, Thursday, 14 September 2006 San Francisco Marriott -- Salon 12/13, Oral

Division of Polymer Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006