文献类型：期刊文献

英文题名：Structural Diversity of the Microbial Surfactin Derivatives from Selective Esterification Approach

作者：Shao, Chuanshi[1,2];Liu, Lin[1,2];Gang, Hongze[1,2];Yang, Shizhong[1,2];Mu, Bozhong[1,2]

机构：[1]E China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[2]E China Univ Sci & Technol, Inst Appl Chem, Shanghai 200237, Peoples R China

年份：2015

卷号：16

期号：1

起止页码：1855

外文期刊名：INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000348403100105)】；

基金：This work was supported by the National Natural Science Foundation of China (Nos. 41073055, 51174092, 41161160560) and the Fundamental Research Funds for the Central Universities of China (No. WF0913005-3).

语种：英文

外文关键词：surfactin; esterification; derivatives; lipopeptide; carboxyl group

摘要：Surfactin originated from genus Bacillus is composed of a heptapeptide moiety bonded to the carboxyl and hydroxyl groups of a beta-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.