Glutathione and N-acetylcysteine inactivations of mutagenic 2(5H)-furanones from the chlorination of humics in water.

摘要: The mutagenic 2(5H)-furanones resulting from the chlorination of lignohumic substances in water disinfection and paper pulp bleaching are known to be inactivated by thiols. objectives present study were characterize kinetics an inactivating reaction, isolate products, determine their mutagenicity relation starting, 2(5H)-furanones. Salmonella typhimurium (TA100) mucochloric acid (MCA) had a mean value 2800 revertants/mumol four assays was twice as potent C-5 isopropyl ether MCA (MCA-IPE), whose determined same assays. A second-order reaction with GSH at pH 7 observed. major product, making up 70% total product mixture, identified 1.5:1 mixture two diastereomers formed sulfur displacement C-4 Cl atom MCA. diastereomer isolated mixture. Connectivity moiety established 2D long-range coupling NMR fully coupled 13C NMR. On basis circular dichroism, S configuration hydroxyl-bearing, ring carbon. MCA-IPE reacted N-acetylcysteine (NAC), giving 1:1 mixtures diastereomers, again single plus NAC reaction. Its structure, X-ray crystallography, 5R,8R agreement ross structure deduced analysis.(ABSTRACT TRUNCATED AT 250 WORDS)