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Analytical HPLC (analytical + hplc)

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Chemistry100%

Selected Abstracts

Design, synthesis and properties of synthetic chlorophyll proteins

FEBS JOURNAL, Issue 11 2001
Harald K. Rau
A chemoselective method is described for coupling chlorophyll derivatives with an aldehyde group to synthetic peptides or proteins modified with an aminoxyacetyl group at the ,-amino group of a lysine residue. Three template-assembled antiparallel four-helix bundles were synthesized for the ligation of one or two chlorophylls. This was achieved by coupling unprotected peptides to cysteine residues of a cyclic decapeptide by thioether formation. The amphiphilic helices were designed to form a hydrophobic pocket for the chlorophyll derivatives. Chlorophyll derivatives Zn-methylpheophorbide b and Zn-methyl-pyropheophorbide d were used. The aldehyde group of these chlorophyll derivatives was ligated to the modified lysine group to form an oxime bond. The peptide,chlorophyll conjugates were characterized by electrospray mass spectrometry, analytical HPLC, and UV/visible spectroscopy. Two four-helix bundle chlorophyll conjugates were further characterized by size-exclusion chromatography, circular dichroism, and resonance Raman spectroscopy. [source]

Synthesis, conformation and biological activity of linear and cyclic Thr6 -bradykinin analogues containing N -benzylglycine in place of phenylalanine,

JOURNAL OF PEPTIDE SCIENCE, Issue 12 2001
L. Biondi
Abstract Three linear Thr6 -bradykinin analogues in which either one or both the two phenylalanine residues in the peptide sequence have been substituted by N -benzylglycine (BzlGly) and their head-to-tail cyclic analogues were synthesized and tested on an isolated rat duodenum preparation. The linear (BzlGly5,Thr6 -BK, BzlGly8,Thr6 -BK and BzlGly5,8,Thr6 -BK) and the cyclic (cyclo BzlGly5,Thr6 -BK, cyclo BzlGly8,Thr6 -BK and cyclo BzlGly5,8,Thr6 -BK) peptoid-like analogues were characterized by amino acid analysis, optical rotation, analytical HPLC and MALDI-TOF mass spectroscopy. The conformational features of both the linear and cyclic derivatives were investigated by FT-IR and CD measurements. Preliminary molecular mechanics calculations were also performed on some synthetic peptides. Pharmacological screening using the relaxation of the isolated rat duodenum preparation showed that incorporation of N -benzylglycine at positions 5 and/or 8 in the linear Thr6 -BK causes a substantial decrease in potency. Comparable incorporation in cyclo Thr6 -BK, at position 8, or 5 and 8, resulted in nearly inactive analogues. However, cyclo BzlGly5,Thr6 -BK showed a potency which is of the same order of magnitude as for cyclo -BK and cyclo Thr6 -BK. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd. [source]

High-performance liquid chromatographic separation and identification of polyphenolic compounds from the infusion of Davilla elliptica St. Hill

PHYTOCHEMICAL ANALYSIS, Issue 1 2008
Clenilson M. Rodrigues
Abstract The isolation of polyphenolic compounds from an infusion of the Brazilian plant Davilla elliptica (Dilleniaceae), used as tea by virtue of its digestive properties, is described. An improved preparative HPLC method was used in order to isolate pure polyphenols from the complex mixture. Liquid,liquid extraction and solid-phase extraction were employed to minimise the interference of polymeric compounds and to provide an enriched fraction of the compounds of interest. The identification of the isolated compounds was performed using analytical HPLC as well as direct injection electrospray ionisation ion trap tandem mass spectrometry (ESI-IT-MS/MS). The high flavonoid content suggests that D. elliptica may be a promising source of compounds to produce natural phytomedicines. Copyright © 2007 John Wiley & Sons, Ltd. [source]

Remarkably Slow Rotation about a Single Bond between an sp3 -Hybridised Carbon Atom and an Aromatic Ring without ortho Substituents

CHEMISTRY - A EUROPEAN JOURNAL, Issue 9 2009
Sarah Murrison
Abstract Look, noorthosubstituents! A series of polycycles were prepared by using a three-component Joullié,Ugi reaction. The rate of rotation about the bond between a highly hindered bridgehead and a phenyl ring with no ortho substituents was measured, and was highly dependent on the substitution. Rotamer half-lives of up to 21,h at 298,K were observed (see figure). Rotamers resulting from this restricted rotation were isolated for the first time. A series of polycycles was prepared by using a three-component Joullié,Ugi reaction. The rate of rotation about the bond between a highly hindered bridgehead and a phenyl ring with no ortho substituents was measured by using, in general, variable-temperature HPLC. The rate of rotation was highly dependent on substitution and rotamer half-lives of up to 21,h at 298,K were observed. Insights into the effect of substitution on the rate of rotation were gleaned through electronic structure calculations on closely related derivatives. Rotamers resulting from restricted rotation about a bond between an sp3 -hybridised carbon atom and a phenyl ring with no ortho substituents were isolated for the first time, and the equilibration of the separated rotamers was followed by using analytical HPLC. It was demonstrated, for the first time, that a highly hindered environment for the sp3 -hybridised atom is sufficient for slow bond rotation about a single bond between sp3 - and sp2 -hybridised carbon atoms. [source]

Developing a New Class of Axial Chiral Phosphorus Ligands: Preparation and Characterization of Enantiopure Atropisomeric Phosphinines

CHEMISTRY - A EUROPEAN JOURNAL, Issue 16 2008
Christian Müller Dr.
Abstract Both enantiomers of the first atropisomeric phosphinine (1) have been isolated by using analytical HPLC on a chiral stationary phase. The enrichment of one enantiomer and a subsequent investigation into its racemization kinetics revealed a barrier for internal rotation of ,=(109.5±0.5),kJ,mol,1, which is in excellent agreement with the theoretically predicted value of ,=116,kJ,mol,1. Further analysis with UV and circular dichroism spectroscopies and density functional theory calculations led to the determination and assignment of the absolute configurations of both enantiomers. These results are the basis for future investigations into this new class of axially chiral phosphinine-based ligands and their possible applications in asymmetric homogeneous catalysis. [source]