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Journal Articles: 34 results
Frank Westheimer's Early Demonstration of Enzymatic Specificity  Addison Ault
Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules.
Ault, Addison. J. Chem. Educ. 2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
The Preparation and Enzymatic Hydrolysis of a Library of Esters  Elizabeth M. Sanford and Traci L. Smith
In this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.
Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ. 2008, 85, 944.
Drugs / Pharmaceuticals |
Enzymes |
Esters |
Industrial Chemistry |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
The Resolution of Ibuprofen, 2-(4′-Isobutylphenyl)propionic Acid  James V. McCullagh
In this experiment the over-the-counter pain reliever ibuprofen is resolved using (S)-(-)-a-phenethylamine as the resolving agent. This procedure has several key advantages over previous resolution experiments.
McCullagh, James V. J. Chem. Educ. 2008, 85, 941.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enantiomers |
Quantitative Analysis |
Separation Science
The Same and Not the Same: Chirality, Topicity, and Memory of Chirality  Wolfgang H. Kramer and Axel G. Griesbeck
Describes a simple molecular approach that aids students in learning stereochemical terms, definitions, and concepts, particularly when chemical structures are drawn in two dimensions.
Kramer, Wolfgang H.; Griesbeck, Axel G. J. Chem. Educ. 2008, 85, 701.
Chirality / Optical Activity |
Stereochemistry
A Simple Laboratory Experiment To Determine the Kinetics of Mutarotation of D-Glucose Using a Blood Glucose Meter  Carlos E. Perles and Pedro L. O. Volpe
A simple commercial blood glucose meter is used to follow the kinetics of mutarotation of D-glucose in aqueous solution. The results may be compared with those obtained using an automatic polarimeter.
Perles, Carlos E.; Volpe, Pedro L. O. J. Chem. Educ. 2008, 85, 686.
Aqueous Solution Chemistry |
Bioanalytical Chemistry |
Carbohydrates |
Chirality / Optical Activity |
Enzymes |
Kinetics |
Solutions / Solvents |
Stereochemistry
Biochemical View: A Web Site Providing Material for Teaching Biochemistry Using Multiple Approaches  Fernanda C. Dórea, Higor S. Rodrigues, Oscar M. M. Lapouble, Márcio R. Pereira, Mariana S. Castro, and Wagner Fontes
Biochemical View is a free, full access Web site whose main goals are to complement existing biochemistry instruction and materials, provide material to teachers preparing conventional and online courses, and popularize the use of these resources in undergraduate courses.
Dórea, Fernanda C.; Rodrigues, Higor S.; Lapouble, Oscar M. M.; Pereira, Márcio R.; Castro, Mariana S.; Fontes, Wagner. J. Chem. Educ. 2007, 84, 1866.
Amino Acids |
Bioenergetics |
Carbohydrates |
Enzymes |
Glycolysis |
Lipids |
Metabolism |
Fatty Acids
A Bioanalytical Chemistry Experiment for Undergraduate Students: Biosensors Based on Metal Nanoparticles  John Njagi, John Warner, and Silvana Andreescu
Describes a laboratory experiment on the development of a biosensor in which students apply electrochemical methods to deposit gold nanoparticles onto electrode surfaces, immobilize an enzyme using glutaraldehyde chemistry, and perform quantitative analysis of phenol using a biosensor with amperometric detection.
Njagi, John; Warner, John; Andreescu, Silvana. J. Chem. Educ. 2007, 84, 1180.
Bioanalytical Chemistry |
Electrochemistry |
Enzymes |
Oxidation / Reduction |
Phenols
Chemical Aspects of General Anesthesia: Part II. Current Practices  Robert Brunsvold and Daryl L. Ostercamp
With the basic elements of balanced general anesthesia in place by the 1950s, the focus turned to developing safer and more effective agents and to improving procedures. During the last half-century a new generation of intravenous induction anesthetics, inhalational anesthetics, and muscle relaxants has emerged.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1826.
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
Chemical Aspects of General Anesthesia: Part I. From Ether to Halothane  Robert Brunsvold and Daryl L. Ostercamp
Summarizes general anesthesia from 1846 to 1956. Events leading up to the adoption of a "balanced" approach, where a sequence of individual compounds is used rather than a single agent, are described.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1821.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
Capsaicin, from Hot to Not; Can New Pain-Relieving Drugs Be Derived from This Substance Known To Cause Pain?  David B. Rusterholz
This article traces the development of modified capsaicin structures that offer improved analgesic effectiveness with minimal pungency and the discovery of compounds that act as antagonists at the TRPV1 receptor, which appear to hold promise as new drugs that will be useful for the treatment of some types of pain.
Rusterholz, David B. J. Chem. Educ. 2006, 83, 1809.
Applications of Chemistry |
Bioorganic Chemistry |
Biosignaling |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Molecular Recognition
Teaching Biologically Relevant Chemistry throughout the Four-Year Chemistry Curriculum  Sarah R. Kirk, Todd P. Silverstein, and Jeffrey J. Willemsen
First-year chemistry students learn introductory chemistry using case studies which deal directly with human health issues and biological processes. Second-year students choose between two equivalent versions of the second-semester course: one that stresses synthetic organic chemistry and another that stresses bioorganic chemistry.
Kirk, Sarah R.; Silverstein, Todd P.; Willemsen, Jeffrey J. J. Chem. Educ. 2006, 83, 1171.
Bioorganic Chemistry |
Bioenergetics
Synthesis and Physical Properties of Liquid Crystals: An Interdisciplinary Experiment  Gerald R. Van Hecke, Kerry K. Karukstis, Hanhan Li, Hansford C. Hendargo, Andrew J. Cosand, and Marja M. Fox
This experiment features an investigative approach designed for the introductory science or engineering major and integrates concepts in the fields of chemistry, biology, and physics. Derived from faculty research interests, this novel experiment gives students the opportunity to draw conclusions from tests performed to illustrate the connection between molecular structure and macroscopic properties. The chemical synthesis of the compounds studied further enhances the connection between molecular structure and macroscopic physical properties. The results of two separate physical measurements, refractometry and absorption spectroscopy, are combined to calculate a microscopic, but very practical, property of chiral nematic liquidsthe pitch of the helix formed in the liquid crystalline phase.
Van Hecke, Gerald R.; Karukstis, Kerry K.; Li, Hanhan; Hendargo, Hansford C.; Cosand, Andrew J.; Fox, Marja M. J. Chem. Educ. 2005, 82, 1349.
Chirality / Optical Activity |
Crystals / Crystallography |
Molecular Properties / Structure |
UV-Vis Spectroscopy |
Acids / Bases |
Esters |
Physical Properties |
Physical Properties
Use of Enzymes in Organic Synthesis: Reduction of Ketones by Baker's Yeast Revisited  James Patterson and Snorri Th. Sigurdsson
The undergraduate organic laboratory Bakers Yeast Reduction of Ethyl Acetoacetate has been improved in two different ways. First, the addition of small quantities of hexane to the aqueous yeast system along with an improved workup protocol has dramatically increased the yield and reproducibility of the ketone conversion to the corresponding alcohol with a high enantiomeric excess. Second, the enantiomeric excess of the alcohol product was ascertained by coupling the alcohol mixture with a chiral acid and analyzing the resulting mixture of diastereomeric esters by proton NMR.
Patterson, James; Sigurdsson, Snorri Th. J. Chem. Educ. 2005, 82, 1049.
Enzymes |
NMR Spectroscopy |
Stereochemistry |
Gas Chromatography |
Synthesis
Chirality Made Simple: A 1- and 2-Dimensional Introduction to Stereochemistry  Robert E. Gawley
Using internal and external reflection elements in one-, two-, and three-dimensional space, the concept of chirality can be introduced in simple terms that are readily understood. Illustrations of 2-D chirality include block letters of the alphabet and the popular video game Tetris. The concepts of 3-D chirality follow logically and can be simplified by projection back to 2-D. Several examples are given, and a PowerPoint presentation of the concepts is available in the Supplemental Material.
Gawley, Robert E. J. Chem. Educ. 2005, 82, 1009.
Chirality / Optical Activity |
Group Theory / Symmetry |
Stereochemistry |
Enantiomers
Protein Design Using Unnatural Amino Acids  Basar Bilgiçer and Krishna Kumar
Using examples from the literature, this article describes the available methods for unnatural amino acid incorporation and highlights some recent applications including the design of hyperstable protein folds.
Bilgiçer, Basar; Kumar, Krishna. J. Chem. Educ. 2003, 80, 1275.
Amino Acids |
Bioorganic Chemistry |
Biotechnology |
Proteins / Peptides |
Synthesis |
Molecular Properties / Structure
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
Put the Body to Them!  Perkins, Robert R.
Examples of chemistry demonstrations involving student participation, including quantized states and systems, boiling point trends, intermolecular vs. intramolecular changes, polar/nonpolar molecules, enantiomers and diastereomers, and chromatography.
Perkins, Robert R. J. Chem. Educ. 1995, 72, 151.
Chromatography |
Physical Properties |
Phases / Phase Transitions / Diagrams |
Molecular Properties / Structure |
Chirality / Optical Activity |
Quantum Chemistry |
Diastereomers |
Enantiomers
Microscale yeast mediated enantiospecific reduction of vanillin, and the absolute configuration of (-)-(R)-[alpha]-deuteriovanillyl alcohol: A bioorganic chemistry experiment   Lee, Moses
An experiment is introduced to a sophomore chemistry course that demonstrates the effeciency and enantiospecificity of microbial/enzyme-mediated reactions and the use of NMR methods in determining the optical activity and absolute configuration of chiral alcohols.
Lee, Moses J. Chem. Educ. 1993, 70, A155.
Enantiomers |
Alcohols |
Bioorganic Chemistry |
Chirality / Optical Activity |
NMR Spectroscopy |
Microscale Lab
An NMR study of the stereochemistry of the fumarase-catalyzed hydration of fumaric acid  Olsen, Julie A.; Olsen, Robert J.
An NMR study of the stereochemistry of the fumarase-catalyzed hydration of fumaric acid.
Olsen, Julie A.; Olsen, Robert J. J. Chem. Educ. 1991, 68, 436.
Acids / Bases |
NMR Spectroscopy |
Enzymes |
Molecular Modeling |
Diastereomers
Binding energy and enzymatic catalysis  Hansen, David E.; Raines, Ronald T.
The authors discuss the fundamental role that the favorable free energy of binding of the rate-determining transition state plays in catalysis and review the principle that many catalytic factors are realized by the use of this binding energy.
Hansen, David E.; Raines, Ronald T. J. Chem. Educ. 1990, 67, 483.
Enzymes |
Catalysis |
Thermodynamics
The enzymatic resolution of aromatic amino acids  Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D.
This article presents an experiment that can demonstrate as many principles of steroisomersim as possible and is also efficient in terms of time and preparation.
Sheardy, Riehard; Liotta, L.; Steinhart, E.; Champion, R.; Rinker, J.; Planutis, M.; Salinkas, J.; Boyer, T.; Carcanague, D. J. Chem. Educ. 1986, 63, 646.
Stereochemistry |
Chirality / Optical Activity |
Enantiomers |
Aromatic Compounds |
Amino Acids |
Enzymes
The catalytic function of enzymes  Splittgerber, Allan G.
Review of the structure, function, and factors that influence the action of enzymes.
Splittgerber, Allan G. J. Chem. Educ. 1985, 62, 1008.
Catalysis |
Enzymes |
Mechanisms of Reactions |
Proteins / Peptides |
Molecular Properties / Structure
Methemoglobinemia: An illness caused by the ferric state  Senozan, N. M.
Hemoglobin's ability to carry oxygen depends on the iron being in the +2 state; methemoglobinemia involves the oxidation of hemoglobin iron to the +3 state.
Senozan, N. M. J. Chem. Educ. 1985, 62, 181.
Proteins / Peptides |
Enzymes |
Medicinal Chemistry |
Oxidation / Reduction |
Oxidation State
Facile assignment of R,S designations to Fischer projections  Price, Howard C.
Suggests a method of assigning R,S designations to Fischer projections that easier than that described in the cited article.
Price, Howard C. J. Chem. Educ. 1980, 57, 528.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
Prochirality and the English beer glass  Sanders, J. K. M.
The English beer glass represents an ideal model for illustrating the concepts of prochirality and assymetric induction.
Sanders, J. K. M. J. Chem. Educ. 1979, 56, 594.
Molecular Properties / Structure |
Chirality / Optical Activity |
Stereochemistry |
Enantiomers
Some aspects of the bioinorganic chemistry of molybdenum  Swedo, Kathleen Bizot; Enemark, John H.
The biological role of molybdenum, biophysical studies of the molybdenum atoms in molybdo-enzymes, and aspects of coordination chemistry that bear on the understanding of molybdo-enzymes.
Swedo, Kathleen Bizot; Enemark, John H. J. Chem. Educ. 1979, 56, 70.
Bioinorganic Chemistry |
Organometallics |
Enzymes |
Coordination Compounds |
Transition Elements
New skeletal-space-filling models. A model of an enzyme active site  Clarke, Frank H.
Reviews the molecular modeling systems available for representing organic and biochemical structures; includes requirements and coordinates for a model of the alpha chymotrypsin active site.
Clarke, Frank H. J. Chem. Educ. 1977, 54, 230.
Molecular Properties / Structure |
Enzymes |
Molecular Modeling |
Molecular Recognition
Simple models for tough concepts  Cavagnol, Richard M.; Barnett, Thomas
One of the most challenging aspects of instructional interaction is the presentation of dynamic chemical concepts interaction is the presentation of dynamic chemical concepts in a way that is both believable and understandable. The authors have devised a series of models that are simple, inexpensive, and require very little time or skill to construct. They allow students to visualize a whole spectrum of phenomena from atomic structure to enzyme-substrate interactions.
Cavagnol, Richard M.; Barnett, Thomas J. Chem. Educ. 1976, 53, 643.
Enzymes |
Molecular Modeling |
Molecular Mechanics / Dynamics |
Atomic Properties / Structure |
Transport Properties
The resolution of racemic acid: A classic stereochemical experiment for the undergraduate laboratory  Kauffman, George B.; Myers, Robin D.
Includes historical background of Pasteur's work and a procedure for investigating the relations between the tartaric acids, racemic acid, and their sodium ammonium salts.
Kauffman, George B.; Myers, Robin D. J. Chem. Educ. 1975, 52, 777.
Stereochemistry |
Molecular Properties / Structure |
Chirality / Optical Activity |
Enantiomers
Complementary rules to define R or S configuration. Viewing molecules from any side  Cori, O.
Reviews the rules to specify the configuration of a chiral center.
Cori, O. J. Chem. Educ. 1972, 49, 461.
Chirality / Optical Activity |
Enantiomers |
Stereochemistry |
Molecular Properties / Structure
Hydrogen sulfide under any other name still smells. A poisonous story  Brasted, Robert C.
The chemistry of hydrogen sulfide affords an excellent opportunity to integrate descriptive inorganic and coordination chemistry with biochemistry.
Brasted, Robert C. J. Chem. Educ. 1970, 47, 574.
Descriptive Chemistry |
Molecular Properties / Structure |
Coordination Compounds |
Enzymes |
Proteins / Peptides
Three-dimensional effects in biochemistry  Ingraham, Lloyd L.
Explores stereospecificity and stereoselectivity; rigidity requirements; steric effects; and stereospecificity when not required mechanistically.
Ingraham, Lloyd L. J. Chem. Educ. 1964, 41, 66.
Molecular Properties / Structure |
Catalysis |
Enzymes |
Molecular Recognition |
Mechanisms of Reactions |
Stereochemistry |
Chirality / Optical Activity |
Enantiomers
Papain as an enzyme catalyst in undergraduate organic chemistry  Abernethy, John Leo; Kientz, Marvin
A rather large number of papain-catalyzed reactions can be selected for use in undergraduate organic laboratory work.
Abernethy, John Leo; Kientz, Marvin J. Chem. Educ. 1959, 36, 582.
Enzymes |
Catalysis