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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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FT-IR spectra of E1, E2 and E3. (A) for the surfactin-C14 and mono-2-methoxy-ethyl-surfactin-C14 ester (E1); (B) for the surfactin-C14 and di-2-methoxy-ethyl-surfactin C14 ester; and (C) for surfactin-C15 and di-2-methoxy-ethyl-surfactin C14 ester.
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ijms-16-01855-f007: FT-IR spectra of E1, E2 and E3. (A) for the surfactin-C14 and mono-2-methoxy-ethyl-surfactin-C14 ester (E1); (B) for the surfactin-C14 and di-2-methoxy-ethyl-surfactin C14 ester; and (C) for surfactin-C15 and di-2-methoxy-ethyl-surfactin C14 ester.

Mentions: FT-IR contradiction between original surfactin and reaction products was described in Figure 7. E1, E2 and E3 showed a significant characteristic transmittance of lipopeptide at the certain wave number. For E1, E2 and E3, there was no strong absorbance around 2610 cm−1, which might relate to carboxylic acid dimmer of Glu and Asp. The absorbance in 1032 cm−1 implied the new ester bond was introduced, which implied that E1, E2 and E3 were surfactin esters.


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)

FT-IR spectra of E1, E2 and E3. (A) for the surfactin-C14 and mono-2-methoxy-ethyl-surfactin-C14 ester (E1); (B) for the surfactin-C14 and di-2-methoxy-ethyl-surfactin C14 ester; and (C) for surfactin-C15 and di-2-methoxy-ethyl-surfactin C14 ester.
© Copyright Policy
Related In: Results  -  Collection

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

ijms-16-01855-f007: FT-IR spectra of E1, E2 and E3. (A) for the surfactin-C14 and mono-2-methoxy-ethyl-surfactin-C14 ester (E1); (B) for the surfactin-C14 and di-2-methoxy-ethyl-surfactin C14 ester; and (C) for surfactin-C15 and di-2-methoxy-ethyl-surfactin C14 ester.
Mentions: FT-IR contradiction between original surfactin and reaction products was described in Figure 7. E1, E2 and E3 showed a significant characteristic transmittance of lipopeptide at the certain wave number. For E1, E2 and E3, there was no strong absorbance around 2610 cm−1, which might relate to carboxylic acid dimmer of Glu and Asp. The absorbance in 1032 cm−1 implied the new ester bond was introduced, which implied that E1, E2 and E3 were surfactin esters.

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