Conversion Between Amino Acid Enantiomers

  • Author: Angewandte Chemie International Edition
  • Published Date: 10 February 2020
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Conversion Between Amino Acid Enantiomers

Amino acids are fundamental building blocks of life. Nearly all living organisms contain structures that are built from L-amino acids, while their mirror-images, the D-configured congeners, are unnatural. D-amino acids have a variety of uses in the pharmaceutical industry and biotechnology, most notably as building blocks of antibiotics. However, their widespread use is hampered by their cost and limited availability. Their synthesis usually involves multi-step procedures.

Jik Chin, University of Toronto, Canada, and colleagues have developed a simple one-step protocol with recyclable auxiliaries that transforms L-amino acids to D-amino acids (or vice-versa) by using differences in solubility between intermediate diastereomeric salts. The team calls the method solubility-induced diastereomer transformation (SIDT).

The intermediate diastereomeric salt was prepared by adding 3,5‐dichlorosalicylaldehyde and a chiral guanidine to a solution of the L-amino acid to create an imino acid salt. This salt rapidly switches between diastereomers. The less soluble diastereomer precipitates cleanly and is then hydrolyzed to give the enantiopure D-amino acid. The auxiliaries can be recovered for further cycles. Throughout the process, only filtration is needed for purification. The proposed method is potentially scalable and generally applicable for a wide variety of amino acids.



Article Views: 1844

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

If you would like to reuse any content, in print or online, from, please contact us first for permission and consult our permission guidance prior to making your request

Follow on Facebook Follow on Twitter Follow on YouTube Follow on LinkedIn Follow on Instagram RSS Sign up for newsletters

Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH