About this ebook
This primer introduces the popular Mosher ester method for determining the stereochemical configurations of secondary alcohols and primary amines bound to a secondary carbon. An introduction to stereochemistry and its importance to the study of natural products is provided, followed by a detailed description of the chemical principles behind the Mosher analysis. Practical aspects of the methodology are also described to provide a starting point for investigators looking to put the technique into practice in a real experimental setting.
Several case studies from the structural analysis of natural products, highlighting different aspects of the Mosher method, are discussed, offering a walk-through of the synthetic methodology, application, and data interpretation. Several such examples have also been selected to demonstrate how the technique can be applied and extended in novel and interesting ways.
By the end of this primer, the reader will not only have a broader understanding of stereochemical analysis but also gain the knowledge necessary to synthesize Mosher esters, apply the derivatization method effectively, and interpret the resulting NMR data to deduce absolute configurations. The reader is encouraged to work through the initial examples in detail and then test their understanding with the case studies presented in the latter sections.
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About the author
Charalambos Michael is a graduate student in the Department of Chemistry at North Carolina State University. He received his BS in chemistry from the University of Cyprus in 2022. His current work lies at the interface of chemistry and biology, focusing on the chemoenzymatic synthesis of bioactive natural products and the elucidation of enzymatic mechanisms under the mentorship of Prof. Wei-chen Chang. His research is directed towards mastering the techniques of organic synthesis and biocatalysis with the goal of developing an integrated approach to novel synthetic strategies for natural products.
Mark W. Ruszczycky earned his bachelor’s degree in biochemistry and master’s degree in chemistry from the University of California, Riverside. He was subsequently admitted to the Medical Scientist Training Program at the Case Western Reserve University School of Medicine in Cleveland, Ohio, where he earned his MD and PhD under the guidance of Vernon E. Anderson. Mark then joined the laboratory of Hung-wen Liu in the Division of Chemical Biology and Medicinal Chemistry in the College of Pharmacy at the University of Texas, Austin, where he continues to study the chemistry of enzyme catalyzed reactions in the biosynthesis of natural products.
Wei-chen Chang earned his bachelor’s degree in agricultural chemistry in 2003 from National Taiwan University under the supervision of Tien-Yau Luh. After a two year mandatory military service, he pursued his PhD in the Medicinal Chemistry Program of the School of Pharmacy at the University of Texas at Austin under the guidance of Hung-wen (Ben) Liu. Wei-chen then joined the laboratory of Marty Bollinger and Carsten Krebs at Pennsylvania State University. He then started his independent career at North Carolina State University, where his group studies the chemistry of enzyme catalyzed reactions in the biosynthesis of natural products as well as enzyme catalysis and engineering.
