13039-40-2Relevant articles and documents
Lipase-catalyzed synthesis of sucrose monolaurate and its antibacterial property and mode of action against four pathogenic bacteria
Shao, Shi-Yin,Shi, Yu-Gang,Wu, Yu,Bian, Li-Qing,Zhu, Yun-Jie,Huang, Xin-Ying,Pan, Ying,Zeng, Lu-Yao,Zhang, Run-Run
, (2018)
The aim of this work was to evaluate the antibacterial activities and mode of action of sucrose monolaurate (SML) with a desirable purity, synthesized by Lipozyme TL IM-mediated transesterification in the novel ionic liquid, against four pathogenic bacteria including L. monocytogenes, B. subtilis, S. aureus, and E. coli. The antibacterial activity was determined by minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and the time–kill assay. SML showed varying antibacterial activity against tested bacteria with MICs and MBCs of 2.5 and 20 mM for L. monocytogenes, 2.5 and 20 mM for B. subtilis, 10 and 40 mM for S. aureus, respectively. No dramatic inhibition was observed for E. coli at 80 mM SML. Mechanism of bacterial inactivation caused by SML was revealed through comprehensive factors including cell morphology, cellular lysis, membrane permeability, K+ leakage, zeta potential, intracellular enzyme, and DNA assay. Results demonstrated that bacterial inactivation against Gram-positive bacteria was primarily induced by the pronounced damage to the cell membrane integrity. SML may interact with cytoplasmic membrane to disturb the regulation system of peptidoglycan hydrolase activities to degrade the peptidoglycan layer and form a hole in the layer. Then, the inside cytoplasmic membrane was blown out due to turgor pressure and the cytoplasmic materials inside leaked out. Leakage of intracellular enzyme to the supernatants implied that the cell membrane permeability was compromised. Consequently, the release of K+ from the cytosol lead to the alterations of the zeta potential of cells, which would disturb the subcellular localization of some proteins, and thereby causing bacterial inactivation. Moreover, remarkable interaction with DNA was also observed. SML at sub-MIC inhibited biofilm formation by these bacteria.
Regioselective synthesis of sucrose monoesters as surfactants
Vlahov, Iontcho R.,Vlahova, Petinka I.,Linhardt, Robert J.
, p. 1 - 10 (1997)
A highly regioselective conversion of sucrose into 6-O-acyl derivatives is reported. First sucrose was transformed into the dibutyltin acetal, thus enhancing the nucleophilicity at the C-6 oxygen and restricting the subsequent acylation reaction. The surface activity properties of the sucrose monoesters obtained were determined and compared with those of commercially available ionic and non-ionic surfactants.
Catalytic selective synthesis method of mono-fatty acid oligosaccharide ester
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Paragraph 0033-0036; 0053-0056, (2020/06/17)
The invention discloses a catalytic selective synthesis method of mono-fatty acid oligosaccharide ester. The method comprises the following steps: adding oligosaccharide, fatty acid or fatty acid ester and a mesoporous catalyst into a reaction solvent, and carrying out mixed reaction; and carrying out filtering, concentrating, recrystallizing and drying to obtain the mono-fatty acid oligosaccharide ester. A multi-phase confinement catalytic selective conversion strategy is adopted, and a series of mono-fatty acid oligosaccharide esters is directly synthesized by appropriately adjusting the acidity or alkalinity and accurately controlling matching of a pore structure and a mono-fatty acid oligosaccharide ester structure, so that the purity and yield are high; and the reaction process is efficient and clean, the refining and purifying process is easy and convenient to operate, energy-saving and environment-friendly, the mesoporous catalyst can be recycled, the performance is kept, the method is suitable for large-scale production, and the toxic residue risk of organic (metal) catalysis and the high cost of biological enzyme catalysis are avoided.
SYNTHESIS AND ACTIVITY OF LACTOSE ESTERS
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Page/Page column 2-3, (2011/10/31)
This disclosure provides for a novel lactose monolaurate (LML) with the structure useful as an antimicrobial agent and as a potential substitute for other sugar esters. Methods of synthesizing LML using immobilize lipases and various solvents are also provided.
