Glutathione-dependent dechlorination of 1,6-dichloro-1,6-dideoxyfructose.
The metabolism of 14C- and 36Cl-labelled 1,6-dichloro-1,6-dideoxyfructose (DCF) was studied in the isolated perfused rat liver system. Dechlorination of DCF occurred in the liver and erythrocytes and was GSH-dependent. The GSH conjugate formed was identified by 13C and 1H n.m.r. as the 6-chlorofructos-1-yl-SG conjugate. It is proposed that the GS- anion attacks the low steady-state concentration of the reactive keto form of DCF and that the conjugate formed cyclizes to the dominant beta-anomer. 6-Chlorofructos-1-yl-SG conjugate of hepatic origin is excreted into bile, whereas that produced in erythrocytes does not enter the liver.
Hughes
H M
HM
Department of Biochemistry, University of Wales College of Cardiff, U.K.
Powell
G M
GM
Snodin
D J
DJ
Daniel
J W
JW
Crawford
A
A
Sanders
J K
JK
Curtis
C G
CG
D000818:Animals; D001646:Bile / Q000378:metabolism; D003837:Deoxy Sugars / Q000378:metabolism*; D005632:Fructose / Q000031:analogs & derivatives* / Q000378:metabolism; D005978:Glutathione / Q000031:analogs & derivatives / Q000378:metabolism*; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D010477:Perfusion; D051381:Rats; D011919:Rats, Inbred Strains
D003837:Deoxy Sugars; C059611:6-chlorofructos-1-yl-glutathione; D005632:Fructose; C059610:1,6-dichloro-1,6-dideoxyfructose; D005978:Glutathione