Dimethylformamide → N-Methyl-D-glucamine

Participants

Reaction Steps

20 g of polifungin and 6 g of glucose were dissolved in 100 ml of dimethyl formamide and allowed to stand at a temperature of 36° C. for 18 hours. The resulting solution was filtered, then 400 ml of 5% ammonium sulphate, aqueous solution, was added to the filtrate and allowed to stand at a temperature of +4° C. for 2 hours. The precipitate was filtered and washed with water and then extracted three times using 800 ml of methanol for each portion. 6 g of N-methylglucamine was dissolved in 60 ml of water and added to the methanol extracts. 1000 ml of n-butanol was added to this solution whereupon the reaction mixture was evaporated at a temperature of 45° C. under reduced pressure to remove methanol and water. The residue was allowed to stand at a temperature of +4° C. for crystallization. The precipitate was filtered and washed with n-butanol, then with petroleum ether and was dried at a room temperature. 16.5 g of the N-methylglucamine salt of the N-glycosyl derivative of polifungin of E1 cm1% =560 at 304 nm and IC50 =0.42 mcg/ml was obtained. Original antibiotic: E1 cm1% =660 at 304 nm and IC50 =0.16 mcg/ml.

Provenance & Evidence