Synthesis of New Glycerolipids Linked to Hydroxamate Derivatives Designed for Two‐Dimensional Crystallization of Aminopeptidase M

Altenburger, Jean-Michel; Lebeau, Luc; Mioskowski, Charles; Schirlin, D.

doi:10.1002/hlca.19920750808

Cited by 14 publications

(13 citation statements)

References 12 publications

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“…A complete esterification of this triacid derivative was performed in methanol with a few drops of sulfuric acid. For the lipid skeleton synthesis, the glycerol moiety was obtained in a one-step procedure by reacting epibromhydrin with 2 equivalents of oleyl alcohol in the presence of NaH, affording the symmetrical dialkylglycerol ether (Altenburger et al, 1992). Acetylation of the 1,3-di-O-oleyl-glycerol with tert-butyl bromoacetate followed by an hydrolysis led to the corresponding acid.…”

Section: Specific Lipidsmentioning

confidence: 99%

Specific Interaction and Two-Dimensional Crystallization of Histidine Tagged Yeast RNA Polymerase I on Nickel-Chelating Lipids

Bischler¹,

Balavoine²,

Milkereit³

et al. 1998

Biophysical Journal

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Nickel-chelating lipid monolayers were used to generate two-dimensional crystals from yeast RNA polymerase I that was histidine-tagged on one of its subunits. The interaction of the enzyme with the spread lipid layers was found to be imidazole dependent, and the formation of two-dimensional crystals required small amounts of imidazole, probably to select the specific interaction of the engineered tag with the nickel. Two distinct preparations of RNA polymerase I tagged on different subunits yielded two different crystal forms, indicating that the position of the tag determines the crystallization process. The orientation of the enzyme in both crystal forms is correlated with the location of the tagged subunits in a three-dimensional model which shows that the tagged subunits are in contact with the lipid layer.

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Section: Specific Lipidsmentioning

confidence: 99%

Specific Interaction and Two-Dimensional Crystallization of Histidine Tagged Yeast RNA Polymerase I on Nickel-Chelating Lipids

Bischler¹,

Balavoine²,

Milkereit³

et al. 1998

Biophysical Journal

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“…These efforts have led to medium resolution structures (i.e. 10 -20 Å ) for RNA polymerase A [12], streptavidin [13 -18], aminopeptidase M [19], DNA gyrase B [20], HupR [21], Moloney murine leukemia virus capsid [2], HIV-1 virus capsid [22], Annexin V [23] and bacterial S-layer [24].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Self-assembly Properties of Acylated Cyclodextrins and Nitrilotriacetic Acid (NTA)-modified Inclusion Ligands for Interfacial Protein Crystallization

Zhou

Haldar

Franses

et al. 2005

Supramolecular Chemistry

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Three different b-cyclodextrins, peracylated on the primary hydroxymethyl rim of the cyclodextrin (6-C n ) 7 b-CD, and nine different nitrilotriacetic acid-modified inclusion ligands (R-NTA) have been prepared and their self-assembly properties characterized. These modular amphiphiles have been developed to promote twodimensional crystallization of proteins at the lipid-water interface. Pressure-area isotherm data suggest that the occupancy of the host sites within the (6-C n ) 7 b-CD monolayers vary as a function of the known host-guest binding constant for the unmodified b-CD host and R guest substituents. Negative-stain TEM experiments show that vesicles are formed upon mild sonication of (6-C 10 ) 7 b-CD and (6-C 16 ) 7 b-CD in 10 mM Tris, pH 7.4 buffer. These results indicate that (6-C n ) 7 b-CD forms stable lyotropic phases that may be useful for templating the interfacial crystallization of histidine-tagged proteins or other molecules capable of interacting with the R-NTA guest ligands.

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“…Trityl groups were removed by acid hydrolysis in anhydrous methanol in the presence of excess p ‐toluenesulfonic acid 35, 36. By this procedure, 4‐(8‐hydroxy‐3,6‐dioxaoctyl‐1‐oxy)‐4′‐cyanoazobenzene and 4‐(11‐hydroxy‐3,6,9‐trioxaundecyl‐1‐oxy)‐4′‐cyanoazobenzene were obtained in 78 and 44% yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and polymerization of amphiphilic methacrylates containing permanent dipole azobenzene chromophores

Altomare

Ciardelli

Gallot

et al. 2001

J. Polym. Sci. A Polym. Chem.

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New amphiphilic photochromic methacrylates with the structures of 4- [methacryloyloxyoligo(ethyleneglycol)]-4Ј-cyanoazobenzene (MEn) and 4-methacryloyloxy-4Ј-{2-cyano-3-oxy-3-[-methoxyoligo(ethyleneglycol)]prop-1-en-1-yl}azobenzene (MEnMe) and oligo(oxyethylene) segments of different lengths were synthesized. These methacrylates were characterized by the presence of permanent dipole azobenzene chromophores and hydrophilic oligo (oxyethylene) segments. The methacrylates were obtained with six-step and five-step synthetic sequences, respectively, in 12-47% overall yields. The radical polymerization of the MEn monomers afforded a 50% yield of the corresponding polymers as orange solids with a number-average molecular weight of about 40 kD. No solid polymer was obtained from the radical polymerization of the MEnME compounds. Two-dimensional NMR spectra allowed the unequivocal assignment of the NMR signals and demonstrated a significant contribution of internal charge transfer to the electronic distribution of the azobenzene chromophore. Relaxation time measurements confirmed that the flexible polyether segment effectively decoupled photochromic groups from the polymer backbone. Optical microscopy, differential scanning calorimetry analysis, and X-ray diffraction data demonstrated the presence of interdigitated smectic mesophases. The stability of mesophases showed a significant dependence on the chemical structure of the analyzed compounds. The glass-transition temperatures of the polymers were rather low because of the plasticizing effect of the spacers. The monomers and polymers were used for the deposition of Langmuir films and Langmuir-Blodgett-Kuhn multilayers. A strong influence of the macromolecular structure on the film properties was observed. The photoresponsive properties of monomers and polymers were investigated with irradiation at different wavelengths. Isomerization kinetics were independent of both molecular weight and spacer length.

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Synthesis of New Glycerolipids Linked to Hydroxamate Derivatives Designed for Two‐Dimensional Crystallization of Aminopeptidase M

Cited by 14 publications

References 12 publications

Specific Interaction and Two-Dimensional Crystallization of Histidine Tagged Yeast RNA Polymerase I on Nickel-Chelating Lipids

Specific Interaction and Two-Dimensional Crystallization of Histidine Tagged Yeast RNA Polymerase I on Nickel-Chelating Lipids

Synthesis and Self-assembly Properties of Acylated Cyclodextrins and Nitrilotriacetic Acid (NTA)-modified Inclusion Ligands for Interfacial Protein Crystallization

Synthesis and polymerization of amphiphilic methacrylates containing permanent dipole azobenzene chromophores

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