Analogues of pantothenic acid

Abstract

I. Five new analogues of pantothenic acid. [gamma]-hydroxy-[beta][beta]-dimethyl-butyry]-[beta]-alanine, [beta][delta]-dihydroxy-[gamma][gamma]-dimethyl-valeryl-[beta]-alanine, [delta]-hydroxy-[gamma][gamma]-dimethyl-[DELTA][alpha][beta]-pen-tenoyl-[beta]-alanine, [gamma]-hydroxy-butyryl-[beta]-alanine and [gamma]-hydroxy-valeryl-[beta]-alanine, were prepared by condensation of the Na salt of [beta]-alanine with the appropriate lactone. Four other analogues were prepared by condensing [alpha]-hydroxy-[beta][beta]-dimethyl butyrolactone with lysine, leucine, valine and taurine. Tested as a growth stimulator for Proteus morgani, none of these had more than a fraction of the effect produced by pantothenic acid. It is proposed to call the radicle CH2OH-C(CH3)2-CHOH[long dash]CO-, the pantoyl group and base upon it a nomenclature for the above compounds. II. Pantoyltaurine (pantothenic acid. except with a sulphonic acid group in place of the carboxy group) was highly inhibitory to Streptococcus haemolyticus and some strains of Corynebacterium diphtheriae, and its effect was reversed by addition of pantothenic acid. Other compounds, some previously described, also had an inhibitory effect on micro-organisms which was not reversed by pantothenic acid. None of these compounds possesses the a-hydroxy group characteristic of pantothenic acid. Hy-droxybutyrylalanine was especially active and inhibited the growth of Streptococcus haemolyticus. C orynebacterium diphtheriae, Bacillus coli, Proteus vulgaris and Staphylo-coccus aureus in high dilution.