Issue 6, 2015
From the journal:

Green Chemistry

A new class of antimicrobial biosurfactants: quaternary ammonium sophorolipids†

E. I. P. Delbeke,a   B. I. Roman,a   G. B. Marin,b   K. M. Van Geemb  and  C. V. Stevens*a  

* Corresponding authors

a SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
E-mail: Chris.Stevens@UGent.be

b LCT, Department of Chemical Engineering and Technical Chemistry, Ghent University, Technologiepark 914, 9052 Ghent, Belgium

Abstract

New synthetic pathways are proposed for the production of a broad range of innovative sophorolipid amines and sophorolipid quaternary ammonium salts starting from microbially produced sophorolipids. The selective formation of an intermediate sophorolipid aldehyde proved to be a key synthetic step of the new derivatives. The sophorolipid quaternary ammonium salts were evaluated for their antimicrobial activity against Gram-negative and Gram-positive test strains. Minimum inhibitory concentration (MIC) values were determined for the active compounds. Derivatives with an octadecyl group on the nitrogen atom proved to be more active than the antibiotic gentamicin sulfate against all tested Gram-positive strains. The results show great promise for modified sophorolipids in the medical sector.

Graphical abstract: A new class of antimicrobial biosurfactants: quaternary ammonium sophorolipids

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Article information

DOI
https://doi.org/10.1039/C5GC00120J
Article type
Paper
Submitted
19 Jan 2015
Accepted
15 Apr 2015
First published
15 Apr 2015

Green Chem., 2015,17, 3373-3377

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A new class of antimicrobial biosurfactants: quaternary ammonium sophorolipids

E. I. P. Delbeke, B. I. Roman, G. B. Marin, K. M. Van Geem and C. V. Stevens, Green Chem., 2015, 17, 3373 DOI: 10.1039/C5GC00120J

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