Organic Chemistry Commons^™

#44 - Introducing Biocatalysis In An Undergraduate Teaching Laboratory Using A Cyclopropanation Reaction, Sarah Youngblood

Georgia Undergraduate Research Conference (GURC)

Introducing Biocatalysis in an Undergraduate Teaching Laboratory Using a Cyclopropanation Reaction

Sarah Youngblood

Faculty Sponsor: Gopeekrishnan Sreenilayam

Biocatalysis is the use of enzymes and proteins to perform chemical transformations. Enzymes and proteins are increasingly used in organic reactions due to excellent chemo-, regio- and stereo- selectivity, environmental sustainability, milder reaction conditions, improved productivity, simplified work-streams and greater economical saving potential. The purpose of this project is to design a biocatalysis experiment that we can incorporate into an undergraduate organic chemistry teaching laboratory. In recent years, there have been a number of studies reported regarding the use of heme containing proteins ...

Photoswitchable Self-Complementary Hydrogen Bond Arrays, Suendues Noori, James A. Wisner

Western Research Forum

Background: Photochromism is the reversible transformation of a chemical material to another form by the absorption of electromagnetic radiation (light), where the two metastable forms have distinct absorption spectra and other properties. Photochromism in materials allows for the switching of their function solely based on irradiation with light. Polymers are used frequently as the building blocks for materials as they are versatile, multifunctional, can carry charge and be processed by solution-based deposition methods. Supramolecular polymers share the same definition as polymers with the exception that they are held together by reversible and directional non-covalent interactions such as hydrogen bonds. Synthesizing ...

Heavy-Atom Tunneling In The Planar Bond Shifting Of [16]Annulene, Philip Lampkin, Jon Shezaf

Creative Activity and Research Day - CARD

Mid-sized annulenes are known to undergo rapid π-bond shifting. Given that heavy­atom tunneling plays a role in planar bond shifting of cyclobutadiene, we computationally explored the contribution of heavy­ atom tunneling to the planar bond shifting in the major (CTCTCTCT) and minor (CTCTTCTT) isomers of [16]annulene. (U)M06-2X/cc-pVDZ calculations yield bond-shifting barriers of ca. 10 kcal/mol. The results also reveal extremely narrow barrier widths, suggesting a high probability of tunneling for these bond-shifting reactions. Rate constants were calculated using canonical variational transition state theory (CVT) as well as with small curvature tunneling (SCT) contributions, via direct ...

Forming Carbon-Carbon Bonds Via Photo-Oxidation, Joseph Pesa, John Rowley

Carroll College Student Undergraduate Research Festival

1-(2-thienyl)-pyrene has been viewed to form a carbon-carbon bond when oxidized. We investigated a palladium catalyzed reaction leading to the dimerization of a furan. However, ostensibly a similar reaction can occur in the absence of palladium but the presence of a photocurrent substantial enough to push an electron to an excited state, leaving a hole in it’s previous orbital. After this occurs, this molecule can find another of the same nature and complete the desired carbon-carbon bond. In creating this bond, we will have synthesized a “solar fuel” that can store energy in a stable bond using ...

Synthesis Of Cyclopropyl Analogs Of Acetylcholine, Douglas Armstrong, Zachary Emptage

Scholar Week 2016 - present

The Ph.D. research by Douglas Armstrong was highly successful for the synthesis of the trans cyclopropyl analog of acetylcholine, but only marginally successful for the cis isomer. In recent years he has developed novel ideas as to how the synthesis of the cis isomer may be improved upon, in ways using more current methods. He has done experiments using some of those methods, and the results, although preliminary, look good.

Synthesis And Optimization Of Novel Poly-(Β-Amino Ester) Polymer For Gene-Delivery, Maria Montes

Kansas State University Undergraduate Research Conference

Gene delivery is one of the most promising methods to treat multiple diseases through the alteration of a genetic code to enhance or inhibit gene expression (NIH). The potential for gene delivery to be used as a treatment for cancerous cells is the beginning for advanced personalized healthcare. Current methods for cancer are costly, nonspecific, and come with major side effects that lowers quality of life in cancer patients. Previous studies have demonstrated Poly-(β-amino ester) (PBAE) to be biodegradable, non-toxic, and capable to deliver payloads in a targeted manner. For this study, PBAE was synthesized and characterized by Nuclear ...

Copper Binding Of Heterocyclic Compounds Is Vital For Novel Drugs Against Gram-Positive Bacteria, Azriel Minjarez-Almeida

Kansas State University Undergraduate Research Conference

Azzy Minjarez1, Man Zhang1, Anjana Delpe-Acharige1, Kayla Eschliman1, Olaf Kutsch2, Stefan H. Bossmann1

1: Department of Chemistry, Kansas State University

2: Department of Medicine, University of Alabama at Birmingham

Copper Binding of Heterocyclic Compounds Is Vital For Novel Drugs Against Resistant Gram-positive Bacteria

Multidrug resistant bacteria are capable of developing resistance to a majority of available antibiotics making them an imminent threat. Thus, synthesizing novel drug candidates is vital. The average adult contains 50-80 mg of copper within the body, which assist the immune system. Efflux pumps of bacterial cells are the primary defense mechanism, which recognize and remove copper ...

Synthesis Of A Sulfur Variant For Treatment Of Trypanosomiasis, Carlos Vera-Esquivel

Student Research and Creative Activity Fair

Previous work in our lab has found diphenyl ether benzylamines showed a successful response with a micromolar concentration of our lead compound to treat the deadly Trypanosamiosis rhodesience. Furthermore, mammalian cell lines saw promising resistance towards damages. The goal of this study was to synthesize a diphenyl thio benzylamine variant. This variant was more active toward T. b. rhodesience but showed more toxicity to both rat 10 (IC₅₀ mM) and human cell lines (HFF, HC-₀₄, U-₂ OS, and HEK₂₉₃). The selectivity index (ratio of toxicity to activity in the same concentration units (SI)) varied from 55 ...