Process improvement in amino acids N-carboxyanhydride synthesis by N-carbamoyl amino acid

Amino acid N-carboxyanhydrides (NCA), convenient monomer for polypeptide synthesis, are easily prepared in high purity as the result of N-carbamoyl amino acids (CAA) nitrosation by gaseous NOx (4:1 NO + O2 mixture, or NOCl) in toluene. Removal of polar side products is then efficiently carried out d...

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Veröffentlicht in:Amino acids 2009, Vol.36, p.341-347
Hauptverfasser: Lagrille, Olivier, Danger, Grégoire, Boiteau, Laurent, Rossi, Jean-Christophe, Taillades, Jacques
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Sprache:eng
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Zusammenfassung:Amino acid N-carboxyanhydrides (NCA), convenient monomer for polypeptide synthesis, are easily prepared in high purity as the result of N-carbamoyl amino acids (CAA) nitrosation by gaseous NOx (4:1 NO + O2 mixture, or NOCl) in toluene. Removal of polar side products is then efficiently carried out during subsequent work-up and crystallisation so that the resulting NCA obtained in good yield is suitable for controlled, primary amine-initiated polymerisation.
ISSN:0939-4451
1438-2199
DOI:10.1007/s00276-008-0090-1