Surfactant and preparation method thereof

A technology of surfactant and surfactant, applied in the field of surfactant and its preparation, can solve the problems of reduced biological activity or interface activity, waste of chemical agents, and non-single product, so as to reduce charge density and improve biological activity and surface activity, the effect of pore film structure stability

Inactive Publication Date: 2012-07-18
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] As can be seen from the above, the esterification method reported in the prior art is mainly the hydrochloric acid catalyzed methyl esterification method, the reaction takes a long time, and the alcohol consumption is large and excessive, which not only causes waste of chemicals but also brings environmental pollution; The side chain includes two carboxylic acid groups, which leads to the existence of two possible structural compounds of monoester and diester in the product obtained by the prior art, and the product is not single; at the same time, the result of monomethylation destroys the saddle shape of surfactin Structural characteristics, while the dimethyl esterification product makes the peptide ring lose two hydrophilic sites on the side chain, resulting in a decrease in biological activity or interface activity

Method used

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  • Surfactant and preparation method thereof
  • Surfactant and preparation method thereof
  • Surfactant and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] In 100mL concentration of 10g / L surfactin (surfactin) in chloroform solution, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) 0.77g while stirring , 4-dimethylaminopyridine (DMAP) 0.049g, 1,6-hexanediol 0.48g (the amount of EDC, DMAP and 1,6-hexanediol is 4 times the molar amount of surfactin). After the feeding was completed, the reaction was stirred at 35° C. for 14 h. After the reaction finished, adopt preparative high performance liquid chromatography separation and purification product surfactin-Glu-, Asp-(6-hydroxyl-hexyl) diester (see figure 1 ), the yield is 97.6%.

Embodiment 2

[0034] In the dichloromethane solution that 100mL concentration is 8g / L surfactin (surfactin), add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) 0.46g while stirring , 4-dimethylaminopyridine (DMAP) 0.029g, 1,6-hexanediol 0.28g (the amount of EDC, DMAP and 1,6-hexanediol is 3 times the molar amount of surfactant). After feeding, the reaction was stirred at 25°C for 19h. After the reaction, the product surfactin-Glu-, Asp-(6-hydroxyl-hexyl) diester was separated and purified by preparative high-performance liquid chromatography, and the yield was 97.4%.

Embodiment 3

[0036] In 100mL concentration of 5g / L surfactant (surfactin) tetrahydrofuran solution, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) 0.19g while stirring, 4 -0.012g of dimethylaminopyridine (DMAP) and 0.12g of 1,6-hexanediol (the amount of EDC, DMAP and 1,6-hexanediol is 2 times of the molar amount of surfactin). After feeding, the reaction was stirred at 18°C ​​for 24h. After the reaction, the product surfactin-Glu-, Asp-(6-hydroxyl-hexyl) diester was separated and purified by preparative high-performance liquid chromatography, and the yield was 97.3%.

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Abstract

The invention provides a surfactant and a preparation method thereof. The method comprises reformation of a surfactin, wherein the reformation of the surfactin comprises the sub-steps of: sequentially adding a 1-ethyl-(3-dimethylaminopropyl) carbonyl diimine hydrochloride catalyst, a 4-dimethylamino-pyridine catalyst and an N-glycol reactant into a surfactin solution; after materials are added, mixing the mixture at 18-35 DEG C for a reaction for 10-30 hours to obtain a surfactin esterification product with hydroxyl; an adding catalysts accounting for 1-10 times by molar weight and the N-glycol accounting for 2-10 times by molar weight into each mole of the surfactin. The preparation method disclosed by the invention has the advantages of complete reaction and little side reaction; and the obtained esterification product has a simple structure. Compared with original surfactin, the surfactin esterification product with the hydroxyl has the advantages of being in higher in surface activity (CMC(Critical Micelle Concentration) is reduced by one order of magnitude), forming a hole-shaped structure on a phospholipid double-layer membrane more efficiently and having a steadier pore membrane structure as well as better biomembrane activity.

Description

technical field [0001] The invention relates to a surfactant and a preparation method thereof, in particular to a modification method of surfactin. Background technique [0002] Lipopeptides are an important class of biosurfactants, which have attracted people's attention due to their excellent surface activity and biological activity. Surfactin is one of the most well-known lipopeptides. In order to improve the surface activity and biological activity of surfactin, scientists have modified the primary structure of surfactin. The methods currently used include lactone ring opening ring, peptide ring amino acid substitution, side chain carboxylic acid group esterification, amidation and total synthesis methods. At present, the more commonly used esterification method mainly adopts the method of Lewis acid catalysis to realize, and its main reaction process is as follows: Surfactant (10mg) is dissolved in the chloroform / methanol (2: 1, v / v) of 20mL, Then, different volumes o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/30C07K7/06C09K23/30
Inventor 牟伯中刘金峰杨世忠邵穿石刚洪泽
Owner EAST CHINA UNIV OF SCI & TECH
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