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Amino Acids

, Volume 18, Issue 3, pp 219–227 | Cite as

The peptides of α-aminosuberic acid I New intermediates for synthetic studies

  • E. Wünsch
  • H. Stocker
  • P. Maloň
  • V. Gut
  • V. Čeřovská
  • M. Žertová
  • D. D. Laffan
  • 48 Downloads

Summary.

The paper describes the synthesis of α-aminosuberic acid derivatives suitable for the synthesis of peptides. These include Z-, Boc- and Fmoc-protection on the α-amino group, benzyl ester, Boc-hydrazide and Z-hydrazide as well as the free carboxylic function in the side chain, and methyl ester, benzyl ester or free α-carboxylic group. Their use is demonstrated on the synthesis of the respective derivatives of Asu-Val-Leu. The enzyme catalyzed reaction was succesfully used both as a route to L-Asu from the D,L-compound as well as for the direct synthesis of the optically active tripeptide derivative from the Z-D,L-Asu-OH.

Keywords:α-Aminosuberic acid – Enzymatic resolution – Peptide synthesis – Synthetic intermediates 

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Copyright information

© Springer-Verlag Wien 2000

Authors and Affiliations

  • E. Wünsch
    • 1
  • H. Stocker
    • 1
  • P. Maloň
    • 2
  • V. Gut
    • 2
  • V. Čeřovská
    • 2
  • M. Žertová
    • 2
  • D. D. Laffan
    • 3
  1. 1. Max-Planck-Institute for Biochemistry, Martinsried, Federal Republic of GermanyDE
  2. 2. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech RepublicCZ
  3. 3. LONZA AG, Research and Development, Visp, SwitzerlandCH

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