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Selective esterification of surfactin: Preparation and properties of surfactin methyl esters



Selective esterification of surfactin: Preparation and properties of surfactin methyl esters



Biotechnology and Applied Biochemistry 20(3): 415-423



The esterification of surfactin by methanolic HCl gave a mixture of two monoesters and a diester. Selective esterification gave surfactin-Glu-gamma-methyl ester as a major compound. These compounds were identified by m.s. and by LiAlH-4 reduction of ester groups. With Asp-beta-methyl ester and Glu-gamma-methyl ester mixture, two association constants with Ca-2+ were found: K = 1.3 times 10-3 M-1 for the aspartic acid residue and K = 2.7 times 10-2 M-1 for the glutamic acid residue. The major monoester, Glu-gamma-methyl ester, has a higher surfactant power than surfactin:31 mN/m instead of 34 mN/m and a much higher haemolytic activity: 12 mu-M instead of 200 mu-M for 100% haemolysis. These differences are discussed and assigned to an increase in the hydrophobic character of surfactin methyl ester.

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Accession: 009392000

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