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Fungal cleavage of thioether bond found in Yperite
Author(s) -
Itoh Noriyuki,
Yoshida Michiko,
Miyamoto Tadashi,
Ichinose Hirofumi,
Wariishi Hiroyuki,
Tanaka Hiroo
Publication year - 1997
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/s0014-5793(97)00812-0
Subject(s) - benzyl alcohol , thioether , chemistry , sulfide , hydrolysis , cleavage (geology) , bond cleavage , organic chemistry , yield (engineering) , degradation (telecommunications) , dimethyl sulfide , alcohol , sulfur , catalysis , materials science , telecommunications , fracture (geology) , computer science , metallurgy , composite material
The degradation of thiodiglycol (I) and benzyl sulfide (II) was attempted using Coriolus versicolor and Tyromyces palustris to investigate the potential ability of basidiomycetes to degrade Yperite (bis(2‐chloroethyl) sulfide), a mass‐produced and stored chemical warfare agent. I was very rapidly degraded by both fungi. The metabolic pathway of II was elucidated, showing that the initial step was the hydrolytic cleavage of the thioether bond to yield benzyl alcohol and benzyl mercaptan. Benzyl alcohol was further oxidized and finally mineralized. Benzyl mercaptan is reversibly converted to benzyl disulfide and also converted to benzyl alcohol. Finally, the effective degradation of bis(2‐bromoethyl) sulfide strongly suggests that basidiomycete would be a potential tool for Yperite degradation.