通过N-氨基甲酰氨基酸亚硝化反应合成氨基酸N-羧基酸酐的工艺改进

Process improvement in amino acid N-carboxyanhydride synthesis by N-carbamoyl amino acid nitrosation.

作者信息

Lagrille Olivier, Danger Grégoire, Boiteau Laurent, Rossi Jean-Christophe, Taillades Jacques

机构信息

Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Université Montpellier 1, Université Montpellier 2, Montpellier, France.

出版信息

Amino Acids. 2009 Feb;36(2):341-7. doi: 10.1007/s00726-008-0090-1. Epub 2008 Apr 15.

DOI:10.1007/s00726-008-0090-1

PMID:18414977

Abstract

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.

摘要

氨基酸N - 羧基酸酐（NCA）是多肽合成中方便使用的单体，通过在甲苯中用气态氮氧化物（4:1的NO + O₂混合物或NOCl）对N - 氨基甲酰氨基酸（CAA）进行亚硝化反应，能够轻松制备出高纯度的NCA。随后在后续的后处理和结晶过程中可以有效地去除极性副产物，从而以良好的产率获得的NCA适用于可控的、由伯胺引发的聚合反应。