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Amino Acids

pp 1–9 | Cite as

Design, synthesis and valued properties of surfactin oversimplified analogues

  • Thaina A. Lima
  • Augusto Etchegaray
  • M. Teresa MachiniEmail author
Original Article

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.

Keywords

Surfactin Synthetic lipopeptides Surface activity Antimicrobial activity Cell anti-adhesion activity Streptococcus mutans 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Informed consent

This is not included as the article does not contain any studies with human participants or animals performed by any of the authors.

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of Biochemistry, Institute of ChemistryUniversity of São Paulo (USP)São PauloBrazil
  2. 2.Center for Life Sciences, Postgraduate Program in Health SciencesPontifical Catholic University of Campinas (PUC-Campinas)CampinasBrazil

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