Search results for "SELE"
showing 10 items of 4721 documents
ChemInform Abstract: New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids.
2010
Racemic and chiral nonracemic α-substituted and α-unsubstituted β-fluoroalkyl β-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained γ-fluorinated β-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral β-enamino esters 4…
Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives
2008
Abstract Chlorosulfonyl isocyanate addition to (−)- and (+)-apopinene furnished monoterpene-fused β-lactams in highly regio- and stereospecific reactions. β-Lactams 5 and 13 exhibited reactivities similar to those of the cycloalkane-fused analogs and were easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis -amino ester afforded the corresponding trans -amino acid enantiomers in excellent yields. The complete isomerization is explained by the stability difference, which was estimated by ab initio calculations between the cis- and trans -diastereomers.
Modelling retention and peak shape of small polar solutes analysed by nano-HPLC using methacrylate-based monolithic columns.
2019
Abstract The development of methacrylate-based monolithic columns was studied for the separation of pharmaceutical hydrophilic compounds in nano-liquid chromatography. The selected polymerisation mixture consisted of 7.5% hexyl methacrylate, 4.5% methacrylic acid and 18.0% ethylene dimethacrylate (w/w), in a binary porogenic solvent (35:35 w/w 1-propanol/1,4-butanediol). The polymer synthesised with this mixture has a good permeability, not excessive back-pressure, and reasonable retention times for polar and non-polar solutes. Monolithic columns (12 cm total capillary length, 100 μm i.d.), prepared with this mixture, were able to produce hydrogen bonding and electrostatic interactions, giv…
Imprinted Polymers for Selective Adsorption of Cholesterol from Gastrointestinal Fluids
1998
A series of highly cross-linked terpolymers of methacryloylated cholesterol or bile acid methyl esters, methacrylic acid, and ethyleneglycol dimethacrylate were prepared in the presence or absence ...
Separation of unmodified α-amino acid enantiomers by reverse phase HPLC
1980
A novel chiral phase system is presented for the resolution of unmodified α-amino acid racemates which is composed of a reverse phase packing coated with N-alkyl-L-hydroxyproline (where alkyl is n-C7H15-, n-C10H21- and n-C16H33-) and a hydro-organic eluent containing copper(II)acetate. The factors controlling retention and enantioselectivity such as concentration of Cu(II)ion and pH of the eluent, addition of NH4Ac to the eluent, type and content of organic solvent of hydro-organic eluent and column temperature were examined. The extremely high enantioselectivity observed (α up to 16) is assumed to be caused by a three site sorbate-sorbent interaction involving bidentate coordination of two…
Polymer-coated reversed-phase packings with controlled hydrophobic properties
1992
Abstract We have designed and synthesized novel reversed-phase packings of non-porous and porous polymethacrylate-coated silicas. By varying the hydrophobicity of the polymer coating, selective unfolding of polypeptides may be achieved, thus enabling manipulation of the chromatographic profile. This study characterizes these packings through their employment for separations of model synthetic peptides of defined secondary, tertiary and quaternary structure. Thus, the packings were applied to the reversed-phase separation α-helical amphipathic and non-amphipathic peptides of the same amino acid composition but different sequences. In addition, selective unfolding of model to-stranded α-helic…
Application of Imprinted Synthetic Polymers in Binding Assay Development
2000
The first part of the review describes a method for the synthesis of molecularly imprinted polymers for use in binding assays. The method considers the many factors involved that affect the recognition properties of the materials and describes an approach to screening and optimization of these factors. The second part describes the development of binding assays using such polymers. This includes the use of different labels, the effect of solvent and buffer, the scale of the assay (amount of solid polymer), and how these influence the quality of the assay in terms of sensitivity, selectivity, and speed of analysis.
Discontinuous electrokinetic chromatography of parabens using different substituted resonances as pseudostationary phases
1999
Resorcarene derivatives, negatively charged even at moderate pH, were synthesized and employed as pseudostationary phases to achieve mobilities exceeding that of the electroosmotic flow. Under these conditions, a discontinuous electrolyte system was developed which allows the separation of four uncharged homologous 4-hydroxybenzoic esters (parabens) within a zone of resorcarene electrolyte, and the detection of these UV active compounds in a resorcarene-free zone, free from the high UV background absorbance of the resorcarenes. Resorcarenes, with differently charged functionalities (carboxylate and phosphate groups) to provide the electrophoretic mobility and with alkyl residues of differen…
Retention behaviour of paracelsin peptides on reversed-phase silicas with varying n-alkyl chain length and ligand density.
1989
As part of further investigations on the characterization of the ligand-induced conformational stabilization of peptides, two series of n-alkyldimethylsilyl bonded silicas have been prepared. In series A the n-alkyl chain length, n, of the bonded phase was varied between 1 and 20 carbon atoms at a constant ligand density. In series B the ligand density, alpha exp, was gradually changed from 0 to 4.1 mumol/m2 on a C1, C4, C6, C8 and C18 bonded phase. The retention behaviour of four peptides of the paracelsin family were examined under isocratic conditions, using a ternary mobile phase of water-methanol-acetonitrile (22:39:39, v/v/v). Plots of k' versus n showed pronounced maxima between n = …
Development of a semiautomated procedure for the synthesis and evaluation of molecularly imprinted polymers applied to the search for functional mono…
2001
Abstract A previously described scaled-down version of the established monolith procedure, where molecularly imprinted polymers (MIPs) are prepared on the bottom surface of chromatographic vials [Anal. Chem. 71 (1999) 2092] has been here further optimised with respect to its full automation. The protocol results in savings of time and reagents compared to the monolith procedure, allowing ca. 60 polymers (∼50 mg each) to be synthesised in parallel. Both blank and imprinted polymers are then evaluated in situ by equilibrium batch rebinding tests. Each step in the synthesis and evaluation was considered with the aim of achieving an automated method with wide applicability with regards to templ…