Syntheses of Phosphonic- and Phosphinic Analogues of Pantothenic Acid Ethyl Ester and of the Phosphonic Analogue of Pantetheine

Article abstract of DOI:10.1002/hlca.19920750809

The replacement of amino acids in peptides by phosphono-analogous (aminoalkyl)phosphonic acids 1, (2-aminoethyl)phosphonic acid (2) and substituted derivatives has been an important aspect of peptides research in the last years.In pantothenic acid (3), there is a peptide linkage between (2R)-2,4-dihydroxy-3,3-dimethylbutyric acid and the amino group of β-alanine, and in pantetheine (4), there is a second peptide linkage between the β-alanine and cysteamine.The synthesis of phosphono and phosphino analogues of pantothenic acid ethyl ester, where the β-alanine is replaced by the diethyl ester of (2-aminoethyl)phosphonic acid and the ethyl ester of (2-aminoethyl)methylphosphonic acid, respectively, and the syntheses of the phosphono analogue of pantetheine, where the β-alanine is replaced by (2-aminoethyl)phosphonic acid, are described.