Bringing research into a first semester organic chemistry laboratory with the multistep synthesis of carbohydrate‐based HIV inhibitor mimics

Abstract

Benefits of incorporating research experiences into laboratory courses have been well documented, yet examples of research projects designed for the first semester introductory organic chemistry lab course are extremely rare. To address this deficiency, a Carbohydrate-Based human immunodeficiency virus (HIV) Inhibitor project consisting of a synthetic scheme of four reactions was developed for and implemented in the first semester organic lab. Students carried out the synthetic reactions during the last 6 of 10 total labs in the course, generating carbohydrate-based dimeric target molecules modeled after published dimers with application in HIV therapy. The project was designed to provide a research experience through use of literature procedures for reactions performed, exploration of variation in linker length in the target structure, and synthesis of compounds not previously reported in the scientific literature. Project assessment revealed strong student support, indicating enhanced engagement and interest in the course as a direct result of the use of scientific literature and the applications of the synthesized carbohydrate-based molecules. Regardless of discussed challenges in designing a research project for the first semester lab course, the finding from data analysis that a project implemented in the first semester lab had significantly greater student impact than a second semester project should provide motivation for development of additional research projects for a first semester organic course.

A 13‐week research‐based biochemistry laboratory curriculum

“…It seems to be a challenge in the superlabs format, where techniques are a priority, to strike a balance between providing a guaranteed success with a pretense of novelty and asking a genuine research question with a possibility of total failure. Perhaps as a consequence, considerable interest in this approach to lab instruction has arisen, evidenced by a spate of recent papers in this journal .…”

Undergraduate research as curriculum

“…Synthesis and screening projects in biochemistry also lend themselves to parallel structuring and student ownership. For example, Boltax, Pontrello, and colleagues have developed two biochemistry CUREs that they have embedded in organic chemistry courses . In one, students synthesize carbohydrate‐based inhibitors of transcription of the human immunodeficiency virus .…”

“…For example, Boltax, Pontrello, and colleagues have developed two biochemistry CUREs that they have embedded in organic chemistry courses . In one, students synthesize carbohydrate‐based inhibitors of transcription of the human immunodeficiency virus . In the other, students design, synthesize, and test potential inhibitors or inducers of polyglutamine protein aggregation, which is a lab model for Huntington's disease .…”

Synthesis of substituted N-phenylmaleimides and use in a Diels–Alder reaction: a green multi-step synthesis for an undergraduate organic chemistry laboratory

“…These experiments provide a variety of approaches to teaching synthesis in the sophomore organic chemistry curriculum with most of them focusing on the synthesis of a biologically (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) or commercially (18)(19)(20)(21)(22)(23)(24) relevant target while some are designed for pedagogical (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) reasons. The complexity of the syntheses differ greatly and range from two (6, 7, 11-13, 16, 18, 20, 22, 27, 31, 36), three (8, 10, 14, 15, 17, 21, 23, 25, 28-30, 34, 37), four (9,26,33,38), five (19,32), six (24,39), and eight (40) step processes. A number of the experiments engage the sophomore organic students in research projects that expose students to the problem-solving skills necessary to optimize and trouble-shoot a multi-step synthesis (38)…”

“…The complexity of the syntheses differ greatly and range from two (6, 7, 11-13, 16, 18, 20, 22, 27, 31, 36), three (8, 10, 14, 15, 17, 21, 23, 25, 28-30, 34, 37), four (9,26,33,38), five (19,32), six (24,39), and eight (40) step processes. A number of the experiments engage the sophomore organic students in research projects that expose students to the problem-solving skills necessary to optimize and trouble-shoot a multi-step synthesis (38)(39)(40)(41) while a couple of experiments ask students to design a synthesis (42,43).…”