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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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Electrospray ionization mass spectrometry (ESI-MS) spectroscopy of B1–B4.
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ijms-16-01855-f004: Electrospray ionization mass spectrometry (ESI-MS) spectroscopy of B1–B4.

Mentions: The ESI-MS spectra of B1, B2, B3 and B4 showed the ionized molecular m/z in Figure 4. For B1, the major m/z peak was 1107, while m/z peak at 1129 could also be found in the same mass spectrum. The difference between the two values was 22. Considering the common positive ionization mode: [M + H]+, [M + Na]+ and [M + K]+, the modes for B1 were [M + H]+ and [M + Na]+. The molecular weight of B1 was 1106, which was equaled to molecular weight calculation value of [Msurfactin-C14 + Mn-hexylalcohol −]. Combined with FT-IR results, B1 was mono-hexyl-surfactin-C14, which derived from surfactin-C14 with one of the carboxylic acid groups esterified by n-hexyl alcohol. The molecular weight of B2 was determined by the same way. B3 had the molecular weight of 1190, which equaled to the molecular weight calculation value of [Msurfactin-C14 + 2 × Mn-hexylalcohol − 2 ×]. The molecular weight of B4 was equaled to molecular weight calculation value of [Msurfactin-C15 + 2 × Mn-hexylalcohol − 2 ×].


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)

Electrospray ionization mass spectrometry (ESI-MS) spectroscopy of B1–B4.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-16-01855-f004: Electrospray ionization mass spectrometry (ESI-MS) spectroscopy of B1–B4.
Mentions: The ESI-MS spectra of B1, B2, B3 and B4 showed the ionized molecular m/z in Figure 4. For B1, the major m/z peak was 1107, while m/z peak at 1129 could also be found in the same mass spectrum. The difference between the two values was 22. Considering the common positive ionization mode: [M + H]+, [M + Na]+ and [M + K]+, the modes for B1 were [M + H]+ and [M + Na]+. The molecular weight of B1 was 1106, which was equaled to molecular weight calculation value of [Msurfactin-C14 + Mn-hexylalcohol −]. Combined with FT-IR results, B1 was mono-hexyl-surfactin-C14, which derived from surfactin-C14 with one of the carboxylic acid groups esterified by n-hexyl alcohol. The molecular weight of B2 was determined by the same way. B3 had the molecular weight of 1190, which equaled to the molecular weight calculation value of [Msurfactin-C14 + 2 × Mn-hexylalcohol − 2 ×]. The molecular weight of B4 was equaled to molecular weight calculation value of [Msurfactin-C15 + 2 × Mn-hexylalcohol − 2 ×].

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