Synthesis of Nepsilon-protected-L-lysine and gamma-benzyl-L-glutamate N-carboxyanhydrides (NCA) by carbamoylation and nitrosation.
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.
Vayaboury
W
W
Université de Montpellier II, UMR 5073 CNRS, Montpellier, France.
Giani
O
O
Collet
H
H
Commeyras
A
A
Schué
F
F
D000812:Anhydrides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D003485:Cyanates / Q000737:chemistry; D018698:Glutamic Acid / Q000737:chemistry; D008239:Lysine / Q000737:chemistry*; D008956:Models, Chemical; D009569:Nitric Oxide / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010100:Oxygen / Q000378:metabolism; D011107:Polylysine / Q000737:chemistry; D011108:Polymers / Q000737:chemistry; D013053:Spectrophotometry; D013696:Temperature
D000812:Anhydrides; D003485:Cyanates; D010080:Oxazoles; D011108:Polymers; D011107:Polylysine; D009569:Nitric Oxide; D018698:Glutamic Acid; D002244:Carbon; C024835:potassium cyanate; D008239:Lysine; D009584:Nitrogen; D010100:Oxygen