Racemization Mechanisms and Chemistry of D-Amino Acids

Photolysis of rac-Leucine with Circularly Polarized Synchrotron Radiation

  1. Uwe J. Meierhenrich1,
  2. Jean-Jacques Filippi1,
  3. Cornelia Meinert1,
  4. Søren V. Hoffmann2,
  5. Jan Hendrik Bredehöft3,
  6. Laurent Nahon4

Article first published online: 16 JUN 2010

DOI: 10.1002/cbdv.200900311

Issue

Chemistry & Biodiversity

Chemistry & Biodiversity

Special Issue: D-Amino Acid Research in Chemistry, Life Sciences, and Biotechnology

Volume 7, Issue 6, pages 1651–1659, June 2010

Additional Information

How to Cite

Meierhenrich, U., Filippi, J.-J., Meinert, C., Hoffmann, S., Bredehöft, J. and Nahon, L. (2010), Photolysis of rac-Leucine with Circularly Polarized Synchrotron Radiation. Chemistry & Biodiversity, 7: 1651–1659. doi: 10.1002/cbdv.200900311

Author Information

  1. 1

    University of Nice-Sophia Antipolis, LCMBA UMR 6001 CNRS, avenue Valrose, F-06108 Nice, (phone: +33-492-076177; fax: +33-492-076151)

  2. 2

    University of Aarhus, Institute for Storage Ring Facilities (ISA), Ny Munkegade 120, DK-8000 Aarhus C

  3. 3

    University of Bremen, Institute for Applied and Physical Chemistry, Leobener Strasse, D-28359 Bremen

  4. 4

    Synchrotron SOLEIL, l'Orme des Merisiers, Saint Aubin BP 48, F-91192 Gif-sur-Yvette

Publication History

  1. Issue published online: 16 JUN 2010
  2. Article first published online: 16 JUN 2010

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Keywords:

  • D-Amino acids;
  • Photolysis;
  • Circularly polarized synchrotron radiation;
  • Synchrotron radiation;
  • Origin of life;
  • Origin of biomolecular homochirality

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Abstract

Amino acids that pass the RNA machinery in living organisms occur in L-configuration. The question on the evolutionary origin of this biomolecular asymmetry remains unanswered to this day. Amino acids were detected in artificially produced interstellar ices, and L-enantiomer-enriched amino acids were identified in CM-type meteorites. This hints at a possible interstellar/circumstellar origin of the amino acids themselves as well as their stereochemical asymmetry. Based upon the current knowledge about the occurrence of circularly-polarized electromagnetic radiation in interstellar environments, we subjected rac-leucine to far-UV circularly-polarized synchrotron radiation. Asymmetric photolysis was followed by an analysis in an enantioselective GC/MS system. Here, we report on an advanced photolysis rate of more than 99% for leucine. The results indicate that high photolysis rates can occur under the chosen conditions, favoring enantioselective photolysis. In 2014, the obtained results will be reexamined by cometary mission Rosetta.

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