Antibacterial Properties of Glycosylated Surfaces: Variation of the Glucosidal Moiety and Fatty Acid Conformation of Grafted Microbial Glycolipids

24 July 2020, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Glycosylated surfaces can display antimicrobial properties. It has been shown that sophorolipids can be used to develop biocidal coatings against Gram-positive and Gramnegative bacteria, but with a limited efficiency so far. Therefore, it appears necessary to further investigate the surface antibacterial activity of a broader set of structurally related glycolipids.
The present work explores the influence of the glucosidic moiety (gluco-, sophoro-, cellobio-)
and the fatty acid backbone (saturated, cis or trans monounsaturated). We show that the fatty
acid backbone plays an important role: cis derivative of sophorolipids (SL) grafted onto model
gold surfaces has better biocidal properties than saturated (SL0) and trans monounsaturated
(SLt) molecules, which appear to be inefficient. The number of glucose units is also a key factor:
a one-third decrease in antibacterial activity is observed when having one glucose unit (GL)
compared to two (SL).Sugar acetylation (SLa) does not seem to have an impact on the biocidal
properties of surfaces. These results are not limited to sophorolipids, cellobioselipids (CL)
leading to similar antibacterial observations.


self-assembled monolayer
antimicrobial surface


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