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Improved synthesis of (S)-N-Boc-5-oxaproline for protein synthesis with the α-ketoacid-hydroxylamine (KAHA) ligation.
Journal article

Improved synthesis of (S)-N-Boc-5-oxaproline for protein synthesis with the α-ketoacid-hydroxylamine (KAHA) ligation.

  • Murar CE Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, CH-8093 Zürich, Switzerland.
  • Harmand TJ Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, CH-8093 Zürich, Switzerland.
  • Bode JW Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, CH-8093 Zürich, Switzerland; Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya 464-8602, Japan. Electronic address: bode@org.chem.ethz.ch.
  • 2017-07-01
Published in:
  • Bioorganic & medicinal chemistry. - 2017
(S)-N-Boc-5-oxaproline
Chemical ligation
Chemical protein synthesis
KAHA ligation
Aldehydes
Hydroxylamines
Magnetic Resonance Spectroscopy
Proline
Proteins
Stereoisomerism
English We describe a new route for the synthesis of (S)-N-Boc-5-oxaproline. This building block is a key element for the chemical synthesis of proteins with the α-ketoacid-hydroxylamine (KAHA) ligation. The new synthetic pathway to the enantiopure oxaproline is based on a chiral amine mediated enantioselective conjugate addition of a hydroxylamine to trans-4-oxo-2-butenoate. This route is practical, scalable and economical and provides decagram amounts of material for protein synthesis and conversion to other protected forms of (S)-oxaproline.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/293232
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