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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 structure of surfactin C13 (R = C4H9), C14 (R = C5H11), C15 (R = C6H13) [7].
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ijms-16-01855-f001: The structure of surfactin C13 (R = C4H9), C14 (R = C5H11), C15 (R = C6H13) [7].

Mentions: Surfactin produced by strains of Bacillus subtilis is one of the most popular lipopeptide and has been studied for tens of years. It is a potent clotting inhibitor and can reduce the surface tension of water to 27 from 72 mN/m [1]. Surfactin is one of the cyclic lipopeptides lactonized by a heptapeptide and a β-hydroxy fatty acid. The typical heptapeptide is l-Glu-l-Leu-d-Leu-l-Val-l-Asp-d-Leu-l-Leu [2,3,4], although there exist some homologues differentiated in their peptide sequence, such as [Val7] surfactin, [Ile7] surfactin [5], [Ala4] surfactin [6], [Asp1, Glu5] surfactin [7]. The β-hydroxy fatty acids are n-, iso-, or anteiso-3-hydroxy fatty with 12–16 carbons [7,8,9]. The representative structure of surfactin is shown in Figure 1.


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 structure of surfactin C13 (R = C4H9), C14 (R = C5H11), C15 (R = C6H13) [7].
© Copyright Policy
Related In: Results  -  Collection

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

ijms-16-01855-f001: The structure of surfactin C13 (R = C4H9), C14 (R = C5H11), C15 (R = C6H13) [7].
Mentions: Surfactin produced by strains of Bacillus subtilis is one of the most popular lipopeptide and has been studied for tens of years. It is a potent clotting inhibitor and can reduce the surface tension of water to 27 from 72 mN/m [1]. Surfactin is one of the cyclic lipopeptides lactonized by a heptapeptide and a β-hydroxy fatty acid. The typical heptapeptide is l-Glu-l-Leu-d-Leu-l-Val-l-Asp-d-Leu-l-Leu [2,3,4], although there exist some homologues differentiated in their peptide sequence, such as [Val7] surfactin, [Ile7] surfactin [5], [Ala4] surfactin [6], [Asp1, Glu5] surfactin [7]. The β-hydroxy fatty acids are n-, iso-, or anteiso-3-hydroxy fatty with 12–16 carbons [7,8,9]. The representative structure of surfactin is shown in Figure 1.

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