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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2015
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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. |
format | Online Article Text |
id | pubmed-4307338 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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