Synthesis of Nepsilon-protected-L-lysine and gamma-benzyl-L-glutamate N-carboxyanhydrides (NCA) by carbamoylation and nitrosation

Amino Acids. 2004 Oct;27(2):161-7. doi: 10.1007/s00726-004-0112-6. Epub 2004 Sep 22.

Abstract

This paper reports on an original process to synthesize N-carboxyanhydrides, which consists of nitrosating N-carbamoylamino acids with a NO/O(2) gas mixture in acetonitrile. The synthesis of several N-carbamoylamino acids of L-lysine was described using potassium cyanate in water. The latter were then nitrosated to yield the corresponding NCA with more or less efficiency. Indeed, the NCA carrying an acid-sensitive protecting group led to a partial deprotection to give the L-lysine NCA salt. The NCA of N(epsilon)-trifluoroacetyl-L-lysine, N(epsilon)-benzyloxycarbonyl-L-lysine and gamma-benzyl-L-glutamate were successfully synthesized with satisfactory yields. Their polymerizability was compared to that of the N(epsilon)-trifluoroacetyl-L-lysine NCA initiated by n-hexylamine in N,N-dimethylformamide. It also showed that this new process of NCA synthesis could be applied to the synthesis of polypeptides and more generally to the protein chemistry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anhydrides / chemistry*
  • Carbon / chemistry*
  • Cyanates / chemistry
  • Glutamic Acid / chemistry
  • Lysine / chemistry*
  • Models, Chemical
  • Nitric Oxide / chemistry
  • Nitrogen / chemistry*
  • Oxazoles / chemistry*
  • Oxygen / metabolism
  • Polylysine / chemistry
  • Polymers / chemistry
  • Spectrophotometry
  • Temperature

Substances

  • Anhydrides
  • Cyanates
  • Oxazoles
  • Polymers
  • Polylysine
  • Nitric Oxide
  • Glutamic Acid
  • Carbon
  • potassium cyanate
  • Lysine
  • Nitrogen
  • Oxygen