A laboratory experiment introducing the concept of chemical bioconjugation of proteins to undergraduate students in a therapeutically relevant context was developed. Initially, students installed an aldehyde functionality into a protein via the oxidation of the N-terminal threonine residue of the cholera toxin subunit B (CTB) protein, which was…

Hands-on learning in a laboratory is an integral part of the undergraduate experience for chemistry students. However, with the onset of the COVID-19 pandemic, an opportunity for this approach was not possible. The pandemic has been forcing instructors to explore the remote setting instead of the laboratory. There are several commercially…

The development of an enzyme-mediated reaction for the first-year general, organic, and biological chemistry (GOB) teaching laboratory is of significant importance so that the factors that affect enzyme-mediated reactions can be adequately demonstrated, reinforcing the lecture portion of the GOB course. Some of the factors that affect these types…

Experiments written for students who were quarantined during the COVID-19 pandemic are described. These were developed to provide hands-on lab experiences that students would not get due to the online nature of course offerings during the crisis. The laboratories described include an extraction and oxidation of aldehydes from food items, a study…

Knowledge of functional groups provides students with a language for organic chemistry. However, students in a health science chemistry course do not plan to be synthetic organic chemists and, therefore, need examples of how functional group chemistry is relevant to their vocational goals. We have developed a lab to demonstrate how simple…

An experimental protocol that provides an excellent way to discuss concepts at the crossroads of organic chemistry and biochemistry employing biocatalysis is presented. By evaluating several reaction parameters (enzyme source, organic solvent, and acyl donor), it was possible to conduct an enzymatic kinetic resolution experiment using…

In this laboratory experiment, upper-division undergraduate chemistry and biochemistry majors investigate amide-bond-forming reactions from a green chemistry perspective. Using hydrocinnamic acid and benzylamine as reactants, students perform three types of amide-forming reactions: an acid chloride derivative route; a coupling reagent promoted…

A laboratory exercise was devised that allows students to rapidly and fairly accurately determine the iodine value of oleic acid. This method utilizes the addition of elemental bromine to the unsaturated bonds in oleic acid, due to bromine's relatively fast reaction rate compared to that of the traditional Wijs solution method. This method also…

Imines are important in biological chemistry and as intermediates in organic synthesis. An experiment for introductory undergraduate organic chemistry is presented in which benzaldehyde was condensed with "p"-methoxyaniline in toluene to give 4-methoxy-"N"-(phenylmethylene)benzenamine. Water was removed by azeotropic…

This inquiry-based experiment is designed for organic or biochemistry undergraduate students to deduce the identity of phospholipids extracted from chicken eggs and dietary supplements. This is achieved using thin-layer chromatography (TLC) data, a series of guided questions of increasing complexity, and provided relative retention factor (Rf)…

A modified total synthesis of (S)-goniothalamin is described for an advanced course in organic chemistry. This experiment gives students an opportunity to handle organometallic reagents and perform an enzymatic kinetic resolution and a metathesis reaction, all in the same synthesis. Furthermore, students learn flame-drying techniques for the…

The Distributed Drug Discovery (D3) program trains students in three drug discovery disciplines (synthesis, computational analysis, and biological screening) while addressing the important challenge of discovering drug leads for neglected diseases. This article focuses on implementation of the synthesis component in the second-semester…

Plants have provided and continue to provide the inspiration and foundation for modern medicines. Natural product isolation is a key component of the process of drug discovery from plants. The purpose of this experiment is to introduce first semester undergraduate organic chemistry students, who have relatively few lab techniques at their…

The organometallic complex Fe[subscript 2](µ-S[subscript 2])(CO)[subscript 6] has interesting biological implications. The concepts of bio-organometallic chemistry are rarely discussed at the undergraduate level, but this experiment can start such a conversation and, in addition, teach valuable synthetic techniques. The lab experiment takes a…

This laboratory experiment gives upper-division organic or biochemistry undergraduate students a comprehensive look at the synthesis, chemical characterization, self-assembly, and secondary structure determination of small, N-acylated peptides inspired by the protein structure of silkworm silk. All experiments can be completed in one 4 h lab…