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Structural diversity of the microbial surfactin derivatives from selective esterification approach.

Shao C, Liu L, Gang H, Yang S, Mu B - Int J Mol Sci (2015)

Bottom Line: 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.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.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 Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Bioreactor Engineering and Institute of Applied Chemistry, East China University of Science and Technology, Shanghai 200237, China. 13641914007@163.com.

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.

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The ratio of (A) monoester-SF and (B) diester-SF in the product in four reaction conditions. Condition 1: catalyzed by 1 mol/L HCl; reacted for 24 h; Condition 2: catalyzed by 1 mol/L HCl; reacted for 48 h; Condition 3: catalyzed by concentrated HCl; reacted for 24 h; Condition 4: catalyzed by concentrated HCl; reacted for 48 h.
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ijms-16-01855-f014: The ratio of (A) monoester-SF and (B) diester-SF in the product in four reaction conditions. Condition 1: catalyzed by 1 mol/L HCl; reacted for 24 h; Condition 2: catalyzed by 1 mol/L HCl; reacted for 48 h; Condition 3: catalyzed by concentrated HCl; reacted for 24 h; Condition 4: catalyzed by concentrated HCl; reacted for 48 h.

Mentions: For HCl catalysis system, it was found that the ratios of monoester-SF and diester-SF in the products varied with the concentration of HCl and the reaction time. Three kinds of n-alcohol were selected to study the relationship between reaction condition and moiety type. Four conditions had been adopted to find regular pattern of the yield, condition 1 (C.1: catalyzed by 1 mol/L HCl; reacted for 24 h), condition 2 (C.2: catalyzed by 1 mol/L HCl; reacted for 48 h), condition 3 (C.3: catalyzed by concentrated HCl; reacted for 24 h) and condition 4 (C.4: catalyzed by concentrated HCl; reacted for 48 h). The ratios of monoester-SF and diester-SF in these four reaction conditions were plotted in Figure 14. The ratio for monoester-SF in the products was C.1 > C.2 > C.3 > C.4, while the ratio order was on the contrary for diester-SF. When the reaction was carried out in the 1 mol/L HCl, it was more inclined to create monoester-SF. For diester-SF concentrated HCl was preferred. Prolonging reaction time from 24 to 48 h was advantageous for the production of diester-SF, but disadvantageous for monoester-SF, which was consistent with Thimon’s report [14]. The results indicated that it was possible to regulate the ratio of surfactin monoester and diester, as well as to obtain specific derivative.


Structural diversity of the microbial surfactin derivatives from selective esterification approach.

Shao C, Liu L, Gang H, Yang S, Mu B - Int J Mol Sci (2015)

The ratio of (A) monoester-SF and (B) diester-SF in the product in four reaction conditions. Condition 1: catalyzed by 1 mol/L HCl; reacted for 24 h; Condition 2: catalyzed by 1 mol/L HCl; reacted for 48 h; Condition 3: catalyzed by concentrated HCl; reacted for 24 h; Condition 4: catalyzed by concentrated HCl; reacted for 48 h.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4307338&req=5

ijms-16-01855-f014: The ratio of (A) monoester-SF and (B) diester-SF in the product in four reaction conditions. Condition 1: catalyzed by 1 mol/L HCl; reacted for 24 h; Condition 2: catalyzed by 1 mol/L HCl; reacted for 48 h; Condition 3: catalyzed by concentrated HCl; reacted for 24 h; Condition 4: catalyzed by concentrated HCl; reacted for 48 h.
Mentions: For HCl catalysis system, it was found that the ratios of monoester-SF and diester-SF in the products varied with the concentration of HCl and the reaction time. Three kinds of n-alcohol were selected to study the relationship between reaction condition and moiety type. Four conditions had been adopted to find regular pattern of the yield, condition 1 (C.1: catalyzed by 1 mol/L HCl; reacted for 24 h), condition 2 (C.2: catalyzed by 1 mol/L HCl; reacted for 48 h), condition 3 (C.3: catalyzed by concentrated HCl; reacted for 24 h) and condition 4 (C.4: catalyzed by concentrated HCl; reacted for 48 h). The ratios of monoester-SF and diester-SF in these four reaction conditions were plotted in Figure 14. The ratio for monoester-SF in the products was C.1 > C.2 > C.3 > C.4, while the ratio order was on the contrary for diester-SF. When the reaction was carried out in the 1 mol/L HCl, it was more inclined to create monoester-SF. For diester-SF concentrated HCl was preferred. Prolonging reaction time from 24 to 48 h was advantageous for the production of diester-SF, but disadvantageous for monoester-SF, which was consistent with Thimon’s report [14]. The results indicated that it was possible to regulate the ratio of surfactin monoester and diester, as well as to obtain specific derivative.

Bottom Line: 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.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.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 Article: PubMed Central - PubMed

Affiliation: State Key Laboratory of Bioreactor Engineering and Institute of Applied Chemistry, East China University of Science and Technology, Shanghai 200237, China. 13641914007@163.com.

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.

Show MeSH
Related in: MedlinePlus