1-(N-Acylamino)alkylphosphonic acids—Deacylation in aqueous solutions

GRAPHICAL ABSTRACT

ABSTRACT

The 1-(N-acylamino)alkylphosphonic acids (AC)-AA^P belong to the interesting and potentially of pharmacological importance group of 1-aminoalkylphosphonic acids derivatives. Since susceptibility of (AC)-AA^P on hydrolytic deacylation can form important factor influencing their biological activity, we have undertaken deacylation investigations of these compounds in aqueous media.

In this article, we present our results on deacylation of various types of 1-(N-acylamino)alkylphosphonic acids (AC)-AA^P, including 1-(N-acetylamino)alkyl-phosphonic Ac-AA^P, 1-(N-chloroacetylamino)alkylphosphonic acids Mca-AA^P, 1-(N-trifluoroacetylamino)alkylphosphonic acids TFA-AA^P, and 1-(N-benzoylamino)-alkylphosphonic Bz-AA^P, derived from representative 1-aminoalkylphosphonic acids AA^P (Gly^P, Ala^P, Val^P, Pgl^P, and Phe^P) in neutral and 2 M HCl solutions.

KEYWORDS:

• Amino acids
• aminophosphonic acids
• 1-aminoalkylphosphonic acids
• 1-(N-acylamino)alkylphosphonic acids
• deacylation
• hydrolytic deacylation

Conflict of interest

The authors declare no competing financial interest.