Detoxification glucoside formation

DE Duggan, JJ Baldwin, BH Arison, RE Rhodes. N-glucoside formation as a detoxification mechanism in mammals J Pharmacol Exp Ther 190(3) 563—569,1974. 

The QSAR data show that glucuronidation can be either a detoxification or bioactivation mechanism, depending chemical structure. For N SAIDs, it appears to be mostly a detoxification mechanism. Nonetheless, the toxicity of acyl glucuronide and glucoside adducts (espedally as it relates to isomerization and protein adduct formation) must be considered when designing carboxylic acids [38]... 

Formation of these amino acid conjugates is catalysed by p-(9-cytokinin)-aIanine synthase, classified as C-N ligase, and characterised in lupin seeds [134]. The enzyme requires O-acetylserine as donor of the alanine moiety and recognises all main cytokinin bases (including BA) and many other purine derivatives as substrates. Similarly to cytokinin 7- and 9-glucosides, also cytokinin 9-alanyl derivatives are biologically inactive and metabolically stable, and are therefore candidates to be cytokinin-inactivation and detoxification products. 

Though less common, formation of N-glycosides also occurs in plants, and direct N-glucosidation of chloramben represents a significant detoxification pathway in tolerant but not in susceptible species." " Susceptibility was associated with the conversion of chloramben to its O-glucose ester as the prominent metabolic route. Subsequently, the N-glucosyltransferase responsible for detoxification of chloramben in tolerant soybean and tomato was isolated and partially characterized." Reference has already been made to the roles of reductive deamination and... 

---