The document describes research into improving catalytic systems for synthesizing phenylalanine derivatives. It summarizes previous work developing cross-coupling reactions using biarylphosphine ligands like SPhos, finding optimal palladium to phosphine ratios of 1:1 yield high product yields with low palladium loadings. New results show the method achieves good yields with para, meta, and ortho-substituted aromatic iodides as well as para- and ortho-substituted aromatic bromides. In conclusions, biarylphosphine ligands are effective for synthesizing phenylalanine derivatives with low catalyst amounts.
Bio-Molecular Engineering is the Future of Molecular BiologyBob Eisenberg
Bio-Molecular Engineering is the Future of Molecular Biology: Now that we have large numbers of excellent structures, we molecular biologists must turn to studying how they work. That is the task of BioMolecular Engineering that uses almost the same tools as classical membrane biophysics. Both treat systems as devices, with inputs, outputs and power supplies, that ONLY function with flow, away from equilibrium.
Bio-Molecular Engineering is the Future of Molecular BiologyBob Eisenberg
Bio-Molecular Engineering is the Future of Molecular Biology: Now that we have large numbers of excellent structures, we molecular biologists must turn to studying how they work. That is the task of BioMolecular Engineering that uses almost the same tools as classical membrane biophysics. Both treat systems as devices, with inputs, outputs and power supplies, that ONLY function with flow, away from equilibrium.
Synthesis, spectroscopic, magnetic properties and superoxide dismutase (SOD) ...IOSR Journals
Three new ternary copper(II) complexes formulated as [Cu(HIda)(bipy)] 1; [Cu(HIda)(phen)] 2; [Cu(HIda)(dmp)] 3; where HIda =N-(2-hydroxyethyl)-2- iminodiacetic acid ; bipy = 2, 2’- bipyridine; phen = 1,10- phenanthroline; dmp = 2,9-dimethyl 1,10-phenanthroline, have been synthesized and characterized by partial elemental analysis, FAB-mass (m/z), EPR, UV-visible and CV measurements. The magnetic and spectroscopic data of all these complexes 1-3 indicate distorted octahedral geometry. The EPR spectra of these complexes in frozen DMSO solutions showed a single at g ca. 2. The trend in g-value (g||>g>2.0023) suggests that the unpaired electron on copper (II) has dx2–y2 character. The SOD activities of the complexes have been investigated. Antibacterial and antifungal activity of these complexes were also measured and discussed.
Saturation of ions in channels and solutions a Fermi-Poisson treatment 11-23-...Bob Eisenberg
Ions in water, and in and near channels, proteins, nucleic acids, and electrodes are difficult to analyze, because everything interacts with everything else through the electric field and through the steric exclusion of ions and water. Ions and water have their own space and cannot overlap significantly. Excluded volume has almost always been treated by enforcing force laws that prevent overlap. Such treatments are difficult to compute because of the singularity of the forces and the need for three dimensions. Here we take a different approach and enforce a Fermi like distribution of the entropy of mixtures of spheres of any size, derived by J.-L. Liu. We show that this approach fits the complex properties of calcium channels, and the properties of gramicdin channels, computed from their full three dimensional structure. Using the simplest shell treatment of hydration, we successfully compute the activity (free energy per mole) curves of pure calcium and sodium chloride solutions. The Fermi-Poisson approach uses the full consistency of its mathematics to replace the computation of repulsive forces. It may prove to be good enough to detail with experimental data in three dimensions difficult to deal with accurately in any other way.
Electrochemical, in-vitro in-vivo study of Co (II)-ofloxacin complexIOSR Journals
Ofloxacin complex has been synthesized and screened for its physicochemical, microbial as well as pharmacological activity have been done in solid and aqueous phase. On the basis of elemental analysis, polarographic studies, amperometric titration and IR spectral studies the probable formula for the complex has been determined at 30±1OC and ionic strength of μ= 1.0[KCl]. Raper’s paper disc method was used for microbial study against various pathogenic bacteria and fungi.Invivo syudy of Swiss mice [25-30gm] were used for antibacterial activity against ofloxacin and its complex on xyline-Alcoholic activity test Kidney, liver and serum of these rats were also studied. On the basis of observed result it could be concluded that Co(II)-Ofloxacin complex were found to be non-toxic and more potent than pure Ofloxacin.(1)
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This module provides an overview of a tool used to gain information on a reaction mechanism; reactive intermediate trapping.
A reactive intermediate is a short-lived, high-energy, highly reactive molecule. When generated in a chemical reaction, it will quickly convert into a more stable molecule. When their existence is indicated, reactive intermediates can help explain how a chemical reaction takes place.
Contributed by:
Shuangyu Ma & Yiling Bi (Undergraduate Students)
University of Utah
2014
Technique that is used to elucidate mechanism of a reaction or in a metabolic pathway and in a cell. The labeling takes place by exchanging a specific atom with their isotope. The detecting of the isotopes in the product helps to understand the possible mechanism and the stereochemistry in this sequence of the reaction. The detection of the isotopic labels is dependent on the kind of isotope. Radioactive isotopes like 3H 14C are measured radiochemical. Stable isotopes like 2H and 13C are detected for example with NMR- and IR-spectroscopy.
Kristina Melnik & Stephanie Felten (Undergraduate Students)
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TMSI promoted 1,4-addition of Copper acetylides to unsaturated aldehydes and ketones.This ppt is totally based on a paper published in Journal of American Chemical Society. The ppt is more about the analysis of the paper
Synthesis, spectroscopic, magnetic properties and superoxide dismutase (SOD) ...IOSR Journals
Three new ternary copper(II) complexes formulated as [Cu(HIda)(bipy)] 1; [Cu(HIda)(phen)] 2; [Cu(HIda)(dmp)] 3; where HIda =N-(2-hydroxyethyl)-2- iminodiacetic acid ; bipy = 2, 2’- bipyridine; phen = 1,10- phenanthroline; dmp = 2,9-dimethyl 1,10-phenanthroline, have been synthesized and characterized by partial elemental analysis, FAB-mass (m/z), EPR, UV-visible and CV measurements. The magnetic and spectroscopic data of all these complexes 1-3 indicate distorted octahedral geometry. The EPR spectra of these complexes in frozen DMSO solutions showed a single at g ca. 2. The trend in g-value (g||>g>2.0023) suggests that the unpaired electron on copper (II) has dx2–y2 character. The SOD activities of the complexes have been investigated. Antibacterial and antifungal activity of these complexes were also measured and discussed.
Saturation of ions in channels and solutions a Fermi-Poisson treatment 11-23-...Bob Eisenberg
Ions in water, and in and near channels, proteins, nucleic acids, and electrodes are difficult to analyze, because everything interacts with everything else through the electric field and through the steric exclusion of ions and water. Ions and water have their own space and cannot overlap significantly. Excluded volume has almost always been treated by enforcing force laws that prevent overlap. Such treatments are difficult to compute because of the singularity of the forces and the need for three dimensions. Here we take a different approach and enforce a Fermi like distribution of the entropy of mixtures of spheres of any size, derived by J.-L. Liu. We show that this approach fits the complex properties of calcium channels, and the properties of gramicdin channels, computed from their full three dimensional structure. Using the simplest shell treatment of hydration, we successfully compute the activity (free energy per mole) curves of pure calcium and sodium chloride solutions. The Fermi-Poisson approach uses the full consistency of its mathematics to replace the computation of repulsive forces. It may prove to be good enough to detail with experimental data in three dimensions difficult to deal with accurately in any other way.
Electrochemical, in-vitro in-vivo study of Co (II)-ofloxacin complexIOSR Journals
Ofloxacin complex has been synthesized and screened for its physicochemical, microbial as well as pharmacological activity have been done in solid and aqueous phase. On the basis of elemental analysis, polarographic studies, amperometric titration and IR spectral studies the probable formula for the complex has been determined at 30±1OC and ionic strength of μ= 1.0[KCl]. Raper’s paper disc method was used for microbial study against various pathogenic bacteria and fungi.Invivo syudy of Swiss mice [25-30gm] were used for antibacterial activity against ofloxacin and its complex on xyline-Alcoholic activity test Kidney, liver and serum of these rats were also studied. On the basis of observed result it could be concluded that Co(II)-Ofloxacin complex were found to be non-toxic and more potent than pure Ofloxacin.(1)
Deciphering reaction mechanism with intermediate trappingDaniel Morton
This module provides an overview of a tool used to gain information on a reaction mechanism; reactive intermediate trapping.
A reactive intermediate is a short-lived, high-energy, highly reactive molecule. When generated in a chemical reaction, it will quickly convert into a more stable molecule. When their existence is indicated, reactive intermediates can help explain how a chemical reaction takes place.
Contributed by:
Shuangyu Ma & Yiling Bi (Undergraduate Students)
University of Utah
2014
Technique that is used to elucidate mechanism of a reaction or in a metabolic pathway and in a cell. The labeling takes place by exchanging a specific atom with their isotope. The detecting of the isotopes in the product helps to understand the possible mechanism and the stereochemistry in this sequence of the reaction. The detection of the isotopic labels is dependent on the kind of isotope. Radioactive isotopes like 3H 14C are measured radiochemical. Stable isotopes like 2H and 13C are detected for example with NMR- and IR-spectroscopy.
Kristina Melnik & Stephanie Felten (Undergraduate Students)
University of Utah
2014
Synthesis, Characterization and Biological Evaluation of Oxazolone Derivativesijceronline
A series of six 4-aryl Benzelidene-2-phenyl-5- oxazolone derivatives were synthesized by condensation of aromatic aldehydes with N-benzoyl glycine (Hippuric acid) in the presence of sodium acetate and acetic anhydride at room temperature in ethanol. Six of the compounds are new derivatives. The structures of the compounds were evaluated based on 1H-NMR , IR and FTIR methods and by elemental analysis. .All the derivative compounds prepared were tested for their antimicrobial activity by disk diffusion technique. Test organisms: Bacteria like Staphylococcus aureusMTCC 7443 and Salmonella typhimuriumMTCC 733 Fungi like C.albicans and A.flavus The results were compared with those of the standard 0.5% Ciprofloxacin. The derivatives with Salicylaldehyde and cinnamaldehyde were showed excellent activities against E. coli. and Staphylococcus aureusMTCC 7443 : than Salmonella typhimuriumMTCC 733 bacteria. It also showed reasonable activity withFungi like C.albicans than A.flavus
1,4- Addition of copper acetylides to unsaturated ketonesSaibalendu Sarkar
TMSI promoted 1,4-addition of Copper acetylides to unsaturated aldehydes and ketones.This ppt is totally based on a paper published in Journal of American Chemical Society. The ppt is more about the analysis of the paper
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A micro-review of the Baeyer-Villiger oxidation with recent (2012/2013) references from the literature; last updated on March 1 2013.
The Baeyer-Villiger Oxidation is a popular tool for the synthesis of esters and lactones.
See an animation at: http://www.harinchem.com/named_organic_reactions.html.
Please send feedback or questions through: http://www.harinchem.com/contactpage.aspx
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Session 2: Synthetic, Structural, and Mechanistic Investigations of Vitamin B12 Conjugates of the Anorectic Peptide PYY3-36
Presenter: Dr. Robert Doyle, Syracuse University & SUNY, Upstate Medical University
Dr. Robert Doyle talks about how vitamin B12 conjugation of Peptide YY3-16 decreases food intake compared to native Peptide – YY3-36 in male rats. Learn how challenges to peptide-based therapies, such as rapid clearance, ready degradation by hydrolysis/proteolysis and poor intestinal uptake and/or a need for blood brain barrier transport can be overcome by using vitamin B12 in the subcutaneously administered drug delivery device iPrecio.
1. Development and understanding of
an improved catalytic system for
the synthesis of phenylalanine
derivatives
Manchester
31st March 2010
Andrew Ross
Prof. Richard Jackson
University of Sheffield
5. Synthesising amino acids
There are 3 main ways to synthesise α amino acids:
• Asymmetric hydrogenation
• Glycine anion alkylation
• Use of the chiral pool
25. Knochel’s work
Knochel, P. et al. J. Org. Chem. 2008, 73, 8422
Uses 2:1 ratio of SPhos to palladium
Uses Pd(II) which needs reducing
26. Preparation of phenylalanine derivatives
• Excess of aromatic iodide used
• Yield calculated based on iodoalanine
• Mass balance made up by protonation
• Standard reaction chosen
44. Conclusions
• Biarylphosphine ligands give high yields of phenylalanine derivatives
•1:1 ratio of Pd:phosphine is optimal
•SPhos gives high yields with low Pd loadings
• High yields can be achieved with para, meta and
ortho substitued aromatics iodides
• Good yields can be achieved with para, and ortho substitued
aromatic bromides
45. Acknowledgments
For the work with aromatic bromides:
Hannah Lang
For help and support:
Prof. Richard Jackson
All the Jackson Group
All the staff at the University of Sheffield
Everybody else who has helped me over the past few years
For Funding:
The University of Sheffield
EPSRC
And thank you for listening