Structure determination of a diuretic-glutathione conjugate by mass and n.m.r. spectrometry.
1. A glutathione (GSH) conjugate of the uricosuric diuretic DBCA 6,7-dichloro-5(N,N-dimethylsulphamoyl)-2,3-dihydrobenzofuran-2-car boxylic acid, formed enzymically in rat liver 100,000g supernatant fortified with GSH, was purified by t.l.c. and h.p.l.c. 2. According to mass spectrometry the composition of the GSH-conjugate corresponded to C21H29N4O11S2Cl2. 1H- and 13C-n.m.r. studies gave the structure of the conjugate as 2-glutathionyl-3-[3,4-dichloro-5-(N,N-dimethyl sulphamoyl)2-hydroxyphenyl]-propionic acid, which indicates that GSH was bound to the chiral centre carbon and caused scission of the C-O bond in the dihydrofuran ring.
Higaki
J
J
Shionogi Research Laboratories, Shionogi & Co., Ltd, Osaka, Japan.
Kikuchi
J
J
Ikenishi
Y
Y
Hirata
M
M
D000818:Animals; D004232:Diuretics / Q000737:chemistry / Q000378:metabolism; D005978:Glutathione / Q000737:chemistry / Q000378:metabolism; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D015394:Molecular Structure; D051381:Rats; D011919:Rats, Inbred Strains; D013449:Sulfonamides / Q000737:chemistry* / Q000378:metabolism
D004232:Diuretics; D013449:Sulfonamides; C052960:S 8666; D005978:Glutathione