Abstract
Surfactins are important lipopeptides produced by Bacillus subtilis that present strong surface activity. These biosurfactants find applications in various fields, from environmental remediation to medicine. The use of surfactins in remediation is hampered by production costs; the medical applications are also reframed because of the hemolytic activity of the cyclic peptide. To reduce costs and working time, the present work focused on the design, chemical synthesis and characterization of simple linear variants of surfactins having only l-amino acids and lauric acid at the N-terminal. Carboxyl-free and amidated analogues with negative, null and positive net charges at physiological pH were successfully obtained. The synthetic isoforms of surfactins showed high surface activity and ability to inhibit both growth and adhesion of Streptococcus mutans cells. Therefore, these properties make these low-cost synthetic peptides relevant and promising new compounds for science, industry and, mainly, dental care.
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Acknowledgements
The authors are grateful to FAPESP for the research grants (2015/14360-4 to MTM and 2013/20570-6 to AE) and post-doctoral fellowship to TAL (2014/06784-6). They also thank CNPq for the research fellowship to MTM (308658/2015) and Dr. Cleber W. Liria for performing the mass spectrometry and amino acid analyses.
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Lima, T.A., Etchegaray, A. & Machini, M.T. Design, synthesis and valued properties of surfactin oversimplified analogues. Amino Acids 52, 25–33 (2020). https://doi.org/10.1007/s00726-019-02806-2
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DOI: https://doi.org/10.1007/s00726-019-02806-2