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Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach

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...

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Autores principales: Shao, Chuanshi, Liu, Lin, Gang, Hongze, Yang, Shizhong, Mu, Bozhong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4307338/
https://www.ncbi.nlm.nih.gov/pubmed/25599527
http://dx.doi.org/10.3390/ijms16011855
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author Shao, Chuanshi
Liu, Lin
Gang, Hongze
Yang, Shizhong
Mu, Bozhong
author_facet Shao, Chuanshi
Liu, Lin
Gang, Hongze
Yang, Shizhong
Mu, Bozhong
author_sort Shao, Chuanshi
collection PubMed
description 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.
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spelling pubmed-43073382015-02-02 Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach Shao, Chuanshi Liu, Lin Gang, Hongze Yang, Shizhong Mu, Bozhong Int J Mol Sci Article 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. MDPI 2015-01-15 /pmc/articles/PMC4307338/ /pubmed/25599527 http://dx.doi.org/10.3390/ijms16011855 Text en © 2015 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Shao, Chuanshi
Liu, Lin
Gang, Hongze
Yang, Shizhong
Mu, Bozhong
Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach
title Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach
title_full Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach
title_fullStr Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach
title_full_unstemmed Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach
title_short Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach
title_sort structural diversity of the microbial surfactin derivatives from selective esterification approach
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4307338/
https://www.ncbi.nlm.nih.gov/pubmed/25599527
http://dx.doi.org/10.3390/ijms16011855
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AT yangshizhong structuraldiversityofthemicrobialsurfactinderivativesfromselectiveesterificationapproach
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