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Int. J. Mol. Sci. 2015, 16(1), 1855-1872; doi:10.3390/ijms16011855

Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach

State Key Laboratory of Bioreactor Engineering and Institute of Applied Chemistry, East China University of Science and Technology, Shanghai 200237, China
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Author to whom correspondence should be addressed.
Academic Editor: Zdenek Wimmer
Received: 6 November 2014 / Accepted: 23 December 2014 / Published: 15 January 2015
(This article belongs to the Section Green Chemistry)
View Full-Text   |   Download PDF [2696 KB, uploaded 15 January 2015]   |  

Abstract

Surfactin originated from genus Bacillus is composed of a heptapeptide moiety bonded to the carboxyl and hydroxyl groups of a β-hydroxy fatty acid and it can be chemically modified to prepare the derivatives with different structures, owing to the existence of two free carboxyl groups in its peptide loop. This article presents the chemical modification of surfactin esterified with three different alcohols, and nine novel surfactin derivatives have been separated from products by the high performance liquid chromatography (HPLC). The novel derivatives, identified with Fourier transform infrared spectroscopy (FT-IR) and electrospray ionization mass spectrometry (ESI-MS), are the mono-hexyl-surfactin C14 ester, mono-hexyl-surfactin C15 ester, mono-2-methoxy-ethyl-surfactin C14 ester, di-hexyl-surfactin C14 ester, di-hexyl-surfactin ester C15, di-2-methoxy-ethyl-surfactin ester C14, di-2-methoxy-ethyl-surfactin ester C15, di-6-hydoxyl-hexyl-surfactin C14 ester and, di-6-hydoxyl-hexyl-surfactin C15 ester. The reaction conditions for esterification were optimized and the dependence of yields on different alcohols and catalysts were discussed. This study shows that esterification is one of the most efficient ways of chemical modification for surfactin and it can be used to prepare more derivatives to meet the needs of study in biological and interfacial activities. View Full-Text
Keywords: surfactin; esterification; derivatives; lipopeptide; carboxyl group surfactin; esterification; derivatives; lipopeptide; carboxyl group
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Shao, C.; Liu, L.; Gang, H.; Yang, S.; Mu, B. Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach. Int. J. Mol. Sci. 2015, 16, 1855-1872.

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