A New Approach to Chiral Enrichment by Exposure of Racemates of Amino Acids to Sonochemically-Prepared BSA Microspheres

Vijay Bhooshan Kumar, Yael Steinberg, Ze'ev Porat, Molhm Nassir, Abed Saady, Alfred Hassner, Aharon Gedanken

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

This preliminary study describes a one-step sonochemical formation of Bovine Serum Albumin (BSA) microspheres and their chiral interaction with several amino acids. Partial separation between enantiomers of various amino acids was accomplished by the interaction of these microspheres with solutions of racemic amino acids. The highest rate of enantiomeric enrichment was attained for D,L-cysteine, where 59% enantiomeric excess (ee) of the L-cysteine was measured. This indicates the preferrential interaction of the BSA microspheres with the D-enantiomer of cystein. No chiral activity was observed for unsonicated BSA molecules. All other D,L-amino acids that were examined provided enrichment of the D-enantiomer albeit in lower ee values. D,L-cysteine interacted with the BSA microspheres leading to L-enantioselective enrichment up to 59 % ee at room tempertaure and 72% at 5 °C. Chiral enrichment was also carried out succesfully with other protein microspheres such as Avidin microspheres. In this case up to 41 % ee was acheived on interaction with DL-phenylalanine. Our simple and facile method opens a new window for enantiomeric separation of racemic compounds.

Original languageEnglish
Pages (from-to)8234-8238
Number of pages5
JournalChemistrySelect
Volume2
Issue number27
DOIs
StatePublished - 21 Sep 2017

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • BSA microspheres
  • DL amino acids
  • chiral enrichment
  • sonochemistry

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