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Asymmetric Synthesis of o- and p-Carboranyl Amino Acids

  • Jonas Malmquist
  • Jörgen Carlsson
  • Karin E. Markides
  • Patrik Pettersson
  • Pär Olsson
  • Kerstin Sunnerheim-Sjöberg
  • Stefan Sjöberg

Abstract

The amino acid p-boronophenylalanine (BPA) containing one boron atom is presently of considerable clinical interest for use in BNCT of cancer. Amino acids, substituted with polyhedral boron clusters, could also be of interest for BNCT.1a–k We have recently reported the synthesis of some amines and optically active amino acids, containing the lipophilic o-carborane cage1b,e In this contribution we describe the synthesis of the hydrophilically substituted o-carborane derivatives, the diolamine 3 (DAC-1) and the diolamino acid 7 (DAAC-1) as well as the asymmetric synthesis of the highly lipophilic amino acid p-carboranylalanine 14. A method for determination of enantiomeric purities of o-carboranylalanine using supercritical fluid chromatography (SFC) on a β-cyclodextrin based stationary phase is reported.

Keywords

Boron Atom Chiral Selectivity Boron Neutron Capture Therapy Asymmetric Synthesis Supercritical Fluid Chromatography 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer Science+Business Media New York 1996

Authors and Affiliations

  • Jonas Malmquist
    • 1
  • Jörgen Carlsson
    • 2
  • Karin E. Markides
    • 3
  • Patrik Pettersson
    • 3
  • Pär Olsson
    • 2
  • Kerstin Sunnerheim-Sjöberg
    • 1
  • Stefan Sjöberg
    • 1
  1. 1.Department of Organic ChemistryUppsala UniversityUppsalaSweden
  2. 2.Department of Radiation SciencesUppsala UniversityUppsalaSweden
  3. 3.Department of Analytical ChemistryUppsala UniversityUppsalaSweden

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