Synthesis of uniformly deuterated n-dodecyl-β-d-maltoside ..

This work reports the first synthesis of uniformly deuterated n-dodecyl-β-d-maltoside (d 39-DDM)
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dodecyl maltoside | Sigma-Aldrich

Small micelle forming detergents are usually favored for crystallizing membrane proteins in order to increase the likelihood of protein-protein interactions. We designed, synthethized and characterized a new class of branch-chained maltoside detergents to customize the micellar properties such as the size and hydrophobicity, for better performance in the stabilization and crystallization of IMPs. The ability to customize the micelle size will be helpful to guide detergent selection and concentration. In addition, the branch-chained maltosides can be easily synthesized and are well-behaved chemically. Thus, they can be readily tested by the community for the crystallization of other IMP targets.

10/07/2012 · We devised an efficient synthesis of four dodecyl trehalosides, ..
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Search results for dodecyl maltoside at Sigma-Aldrich

The choice of detergent is a critical parameter for successful crystallization of integral membrane proteins. We and others have often observed that the alkyl-chain length of a detergent is crucial for stabilizing and crystallizing IMPs—even one-carbon change can have dramatic effects. Our data using branch-chained maltosides for solubilization, stabilization and crystallization of Cx26 imply that a shorter chained detergent with optimized hydrophobicity can perform as well or better than the longer chained analogues.

Lipid Products | n-dodecyl-ß-D-maltoside (DDM) | 850520
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Sugar-based detergents, mostly derived from maltose or glucose, prevail in the extraction, solubilization, stabilization and crystallization of membrane proteins. Inspired by the broad use of trehalose for protecting biological macromolecules and lipid bilayer structures, we synthesized new trehaloside detergents for potential applications in membrane protein research. We devised an efficient synthesis of four dodecyl trehalosides, each with the 12-carboned alkyl chain attached to different hydroxyl groups of trehalose, thus presenting a structurally diverse but related family of detergents. The detergent physical properties, including solubility, hydrophobicity, critical micelle concentration (CMC) and size of micelles, were evaluated and compared with the most popular maltoside analog, β- D-dodecylmaltoside (DDM), which varied from each other due to distinct molecular geometries and possible polar group interactions in resulting micelles. Crystals of 2-dodecyl trehaloside (2-DDTre) were also obtained in methanol, and the crystal packing revealed multiple H-bonded interactions among adjacent trehalose groups. The few trehaloside detergents were tested for the solubilization and stabilization of the nociceptin/orphanin FQ peptide receptor (ORL1) and MsbA, which belong to the G-protein coupled receptor (GPCR) and ATP-binding cassette transporter families, respectively. Our results demonstrated the utility of trehaloside detergents as membrane protein solubilization reagents with the optimal detergents being protein dependent. Continuing development and investigations of trehaloside detergents are attractive given their interesting and unique chemical-physical properties and potential interactions with membrane lipids.

Custom Synthesis; Print; n-dodecyl-ß-D-maltoside ..
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Dodecyl maltoside synthesis essay - …

The hydrodynamic radius (Rh) of micelles formed by each detergent was measured using dynamic light scattering (). 3-DDTre, 6-DDTre and DDM micelles are similar in size with mean radii of 3.3, 3.4 and 3.4 nm, respectively, and their size distribution is similar as well, which suggest a similar packing of monomers in the micelles for the three detergents. However, 2-DDTre forms much smaller micelles (Rh = 2.9 nm) indicative of a larger surface curvature. Interestingly, 4-DDTre forms the largest and most polydisperse micelles. The different micellar properties are a reflection of the distinct molecular geometry of the four DDTre and DDM molecules, and are potentially affected by hydrophilic interactions between the sugar units.

n-Dodecyl-beta-D-maltoside CAS#: 69227-93-6

The CMC values of 2-DDTre, 3-DDTre, 4-DDTre, and 6-DDTre, measured in water using a fluorescence dye (ANS) incorporation assay, are 0.018% (0.35 mM), 0.024% (0.47 mM), 0.009% (0.18 mM), and 0.007% (0.14 mM), respectively (). Since the formation of detergent micelles is driven mainly by hydrophobic association, the hydrophobicity is usually inversely correlated with the CMC value. However, this is not exactly the case for DDTre molecules and DDM. For example, the CMCs for 4-DDTre, 6-DDTre and DDM (0.008%, 0.16 mM) are about the same, but the hydrophobicity measurements differ largely as shown above. We assume that the interaction between polar groups also plays a significant role in the micelle formation of these sugar detergents. We also noted that the ANS fluorescence curves in differ in the slope above the CMC of each detergent, which might indicate changes in total concentration and/or microenvironment of ANS molecules that partition into the different micelle solutions.

Watson International Ltd develops n-Dodecyl-beta-D-maltosid ..

DDM is the most popular commercial detergent for the solubilization of many human G-protein coupled receptors (GPCRs) and transporters. We evaluated the new DDTre detergents on the solubilization and stabilization of the nociceptin/orphanin FQ peptide receptor, ORL1, a member of opioid receptor family, and EcMsbA, a member of ATP-binding cassette (ABC) transporters. The structure of ORL1 containing the N-terminal fusion protein b562RIL (BRIL-ORL) has most recently been determined using the protein material purified in the DDM-cholesterol hemisuccinate (CHS) mixture and in meso phase crystallization technique. Several MsbA homolog proteins including EcMsbA have been crystallized in maltoside detergents and structurally determined at moderate resolutions.