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Synfacts 2007(4): 0374-0374  
DOI: 10.1055/s-2007-968309
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Ring-Opening Metathesis Polymerization of Lactonic Sophorolipids

Contributor(s): Timothy M. Swager, Wei Zhang
W. Gao, R. Hagver, V. Shah, W. Xie, R. A. Gross*, M. F. Ilker, C. Bell, K. A. Burke, E. B. Coughlin
Polytechnic University, New York, USA
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

The natural bioactive glycolipid, sophorolipid (1) was polymerized to semicrystalline poly(sophorolipid) (2) by ring-opening-meta­thesis polymerization (ROMP) using a ruthenium catalyst. Sophorolipid monomer was obtained through fermentation of Candica bombicola. The poly(sophorolipid) was formed in high yield up to 89% with Mn up to 103,000. It was proposed that strong intermolecular interactions between poly(sophorolipid) molecules enthalpically drive the facile polymerization of low-ring-strain 26-membered sophorolipid monomer.