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Chirality and the Origins of Life

A Case Study in Organic Chemistry

Co Authors:

Michael C. Young
Department of Chemistry
University of California, Riverside

Richard J. Hooley
Department of Chemistry
University of California, Riverside


In this case study, students are guided through an example of how the amplification of enantiomeric excess in prebiotic amino acids may have contributed to the occurrence of only L-amino acids in nature. By studying the mechanism of racemization of amino acids and their derivatives and applying the concepts of crystallization and equilibrium, students can critically analyze a recent (2008) article in the Journal of the American Chemical Society on chirality enhancement under conditions that mimic the prebiotic environment. The article provides a possible cause of single enantioforms of amino acids, and the case study extends this to critically investigate whether this is a viable theory for the existence of L amino acids as the sole natural constituents of natural macromolecules. This case study is designed for a first semester/first quarter organic chemistry course, and is generally presented in the middle of the course after the topics of stereochemistry and acid/base reactions are taught.

  • Highlight the relevance of chemistry to current world issues.
  • Apply basic organic chemistry knowledge to complex, multi-faceted problems.
  • Develop the ability to critically analyze primary literature and draw conclusions based on the data and evidence contained therein.
  • Develop the ability to communicate scientific and technical concepts in both written and verbal form to both technical and non-technical audiences.
  • Assist in the development of fundamental organic chemistry skills such as stereochemistry and mechanism.
Keywords: Organic reactions; racemization; stereochemistry; amino acids; origins of life
Topical Area: N/A
Educational Level: Undergraduate lower division
Formats: PDF, PowerPoint
Type/Method: Analysis (Issues), Discussion, Journal Article
Language: English
Subject Headings: Organic Chemistry  
Date Posted: 11/6/2014
Date Modified: N/A
Copyright: Copyright held by the National Center for Case Study Teaching in Science, University at Buffalo, State University of New York. Please see our usage guidelines, which outline our policy concerning permissible reproduction of this work.

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