Hydrazinolysis Products of Selected Sugar Lactones—Crystal Structure and Microbiological Activity

Abstract

Commercially available lactones, as well as those synthesized by us, turned out to be good substrates for the synthesis of sugar hydrazides. The exception was L-ascorbic acid, whose hydrazinolysis led to the formation of a hydrazinium salt, not the hydrazide as expected. The structure of all compounds was confirmed by NMR and X-ray analyses. The lower durability of hydrazinium L-ascorbate was additionally confirmed by thermogravimetric tests. All products were tested for biological activity against Gram-negative bacteria strains Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853 and against Gram-positive Staphylococcus aureus ATCC 25923 and Staphylococcus aureus ATCC 29213. Their antifungal activity against Candida albicans SC5314, Candida glabrata DSM 11226 SM 11226, Candida krusei DSM 6128, and Candida parapsilosis DSM 5784 was also tested. The most interesting results of microbiological activity were obtained for D-gluconic acid hydrazide and hydrazinium L-ascorbate. The results of the latter encourage more extensive testing.