Structural studies on sucrose monolaurate

York, William C.; Finchler, Arthur; Osipow, Lloyd; Snell, Foster Dee

doi:10.1007/bf02630773

Cited by 25 publications

(9 citation statements)

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“…The sucrose monoester, β-D-Fructofuranosyl-6-O-myristyl-α-D-glucopyranoside (MMS), was synthesized by a modification of the Osipow-Snell method (Osipow et al 1956; York et al1956) that yields a relatively complex mixture of mono- (mainly 6-O and presumably 1-O), di and tri-esters. To isolate the monoester, a chromatographic procedure previously described was employed (Becerra et al 2006) The NMR spectra, obtained on a Bruker ADX 300 spectrometer, with DMSO d-6 containing 5% of CH 3 OD to avoid micellization, are in good agreement with previously reported spectra of monoesters (Vlahov et al 1997).…”

Section: Methodsmentioning

confidence: 99%

Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size

Toro

Sánchez

Zanocco

et al. 2009

Chemistry and Physics of Lipids

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The solubilization of biological membranes by detergents has been used as a major method for the isolation and purification of membrane proteins and other constituents. Considerable interest in this field has resulted from the finding that different components can be solubilized selectively. Certain membrane constituents are incorporated into small micelles, whereas others remain in the so-called detergent-resistant membrane domains that are large enough to be separated by centrifugation. The detergent resistant fractions contain an elevated percentage of cholesterol, and thus its interaction with specific lipids and proteins may be key for membrane organization and regulation of cellular signaling events.This report focuses on the solubilization process induced by the sucrose monoester of myristic acid, β-D-Fructofuranosyl-6-O-myristyl-α-D-glucopyranoside (MMS), a nonionic detergent. We studied the effect of the head group and the cholesterol content on the process. 1-Palmitoyl-2-oleoyl-snglycero-3-phosphocholine (POPC) and Dioctadecyl dimethylammonium chloride (DODAC) vesicles were used, and the solubilization process was followed using Laurdan (6-Dodecanoyl-2-dimethylaminonaphthalene) Generalized Polarization (GP) measurements, carried out in the cuvette and in the 2-photon microscope.Our results indicate that: (i) Localization of the MMS moieties in the lipid bilayer depend on the characteristics of the lipid polar head group and influence the solubilization process. (ii) Insertion of cholesterol molecules into the lipid bilayer protects it from solubilizaton and (iii) the microscopic mechanism of solubilization by MMS implies the decrease in size of the individual liposomes.

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Section: Methodsmentioning

confidence: 99%

Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size

Toro

Sánchez

Zanocco

et al. 2009

Chemistry and Physics of Lipids

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“…A quantitative procedure to evaluate ester distribution and isomer formation was developed by Weiss and coworkers using thin-layer chromatography (18). Nearly 80% of the esterification takes place on the glucosyl residue of sucrose (34). Moreover, the carbon at the C-6 or primary hydroxyl position is now known to be most frequently involved although both C-4 and C-1 positions show a moderate amount of substitution (35).…”

Section: Sucrose Estersmentioning

confidence: 99%

Carbohydrate‐alkyl ester derivatives as biosurfactants

Allen

Tao

1999

J Surfact & Detergents

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Reaction of carbohydrates with long-chain plantderived lipids yields carbohydrate-alkyl ester surfactants with a polyol structure. Their renewability, low cost, and environmental acceptability make carbohydrate-alkyl ester surfactants an excellent alternative to petrochemically derived products. This article reviews developments in the synthesis and surface-active properties of carbohydrate-alkyl ester surfactants.Paper no. S1150 in JSD 2, 383-390 (July 1999). KEY WORDS:Biosurfactants, carbohydrate esters, sugar esters.Surfactants are critical to the cleaning, emulsifying, wetting, and foaming properties of many products. Surfactants are found in a host of applications, including cosmetics, textiles, pharmaceuticals, foods, ore flotation, soaps and detergents, pulp and paper manufacturing, lubricating and metalworking, agrichemicals, and petroleum mining fields. In most industrial cases, surfactants are used as processing aids and are disposed of following usage. Issues regarding disposal have created interest in more biologically acceptable alternatives and more focused use of renewable vs. nonrenewable resources.In this context, carbohydrate-based surfactants are gaining attention. Carbohydrates in the form of polysaccharides are produced naturally in plants and account for approximately three-quarters of the dry weight of the biological world and nearly 80% of the human caloric diet (1). Corn, potatoes, tapioca, and wheat are currently processed and constitute common sources of starch. Polysaccharides are of interest because of the number of reactive hydroxyl groups they carry. Condensation of one of the reactive groups of a saccharide with a fatty acid produces a surfactant. The saccharide provides the hydrophilic component, whereas the fatty acid provides the hydrophobic component. Various types of saccharides that have been used to furnish the required hydrophilicity are outlined in Scheme 1. Carbohydrate-based surfactants have been used primarily in the cosmetic, detergent, food, and pharmaceutical industries (2-4) as they are physiologically, dermatologically, and biologically acceptable (5,6). Because they are odorless, tasteless, nonionic, and biodegradable, they compare well in overall performance (i.e., emulsification, detergency, foam power, wetting power, and other related properties) with other surface-active compounds (7).To date, several major types of carbohydrate-based surfactants are used worldwide. Sucrose esters and sorbitan esters as well as other carbohydrate derivatives are highlighted here. SUCROSE ESTERSSucrose esters are synthesized primarily by combining the primary hydroxyl group of the nonreducing glucose moiety with a methyl ester of a fatty acid (Scheme 2). Synthesis of sucrose fatty acid derivatives was first considered by Herzfeld in 1880 (5). Sucrose octaesters were later synthesized and their physical properties measured (8,9). In 1924, a patent disclosing the condensation of fatty acid chlorides with sucrose in pyridine was awarded to Rosenthal (5), and in 1950 Zief (10) desc...

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“…The results obtained provide useful information about the effect the bulky hydrophilic head, the sucrose moiety and on the influence of the effect of the lipophillic hydrophilic balance on the capacity of these compounds to saturate and solubilize DDPC vesicles. 23,24 that yields a relatively complex mixture of mono-(mainly 6-O and presumably 1-O), diand tri-esters. To isolate monoesters, chromatography on silica column was employed.…”

Section: Introductionmentioning

confidence: 99%

Solubilization of DPPC Small Unilamellar Liposomes by Sucrose Esters: A Fluorescence Study

Berrios

Zanocco

Lemp

et al. 2008

J. Chil. Chem. Soc.

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The effect of the microenvironment on the Laurdan fluorescence was employed to study the solubilization mechanism of Dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) small unilamellar vesicles with several sucrose monoesters. The saturation and the solubilization concentrations (C sat and C sol ), the ester-DPPC molar ratio (R e ) and the bilayer/aqueous partition coefficients (K) were measured by monitoring changes in laurdan generalized polarization for four different alkyl esters of sucrose. All critical concentrations showed linear dependence with DPPC liposomes concentration. The saturation and the solubilization capacity of this type of surfactant do not show a direct dependence with the length of its alkyl chain. For the studied series the lauryl sucrose derivative is the compound which presents the higher capacity to saturate and solubilize the DPPC vesicles, while the capacity of the esters with shorter and longer alkyl chains worsen. When the results obtained for DPPC liposomes are compared with previously obtained data for DODAC a different structuration of sucrose moieties in the bilayer can be postulated.

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Structural studies on sucrose monolaurate

Abstract: Conclusion A product corresponding to sucrose monolaurate was prepared by the alcoholysis of methyl laurate with sucrose. This product appears to be a mixture, with the principal component having the lauroyl radical at the 6‐position of the glucose portion.

Cited by 25 publications

References 1 publication

Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size

Solubilization of lipid bilayers by myristyl sucrose ester: effect of cholesterol and phospholipid head group size

Carbohydrate‐alkyl ester derivatives as biosurfactants

Solubilization of DPPC Small Unilamellar Liposomes by Sucrose Esters: A Fluorescence Study

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