Glucosides formation

Glucoside formation from alcohols, phenols, and carboxylic acids... 

A series of 36 plants showed only two that form no glucosides when sucrose is injected into the leaves. In the two exceptions, the sucrose was converted into nonsugars. Phosphorylation uncouplers (2,4-dinitrophenol, iodoacetate, and the like) did not affect o-glucoside formation.226... 

In 1945, Hurd and Bonner129 130 reported the reaction of either tetra-O-acetyl-a-D-glucopyranosyl chloride or penta-0-acetyl-/3-D-glucopy-ranose with benzene in the presence of aluminum chloride, to form 1,2-/rans-/3-D-glucopyranosylbenzene. The implication of the above results (on /3-D-glucoside formation) in connection with the nature of this latter reaction is obvious. 

Hezari, M., Davies, P.J. Microbial models of mammalian metabolism. Furosemide glucoside formation using the fungus Cunninghamella elegans. Drug Metab. Disp. 1993, 21 259-267. 

GMELIN, R., VIRTANEN, A.I., A new type of en2ymatic cleavage of mustard oil glucosides. Formation of allylthiocyanate in Thlaspi arvense L. and benzylthiocyanate in Lepidium ruderale L. and Lepidium sativum L., Acta Chem. Scand., 1959, 13, 1474-1475. 

These facts indicate that (H-)-maltose has structure I, which is given the name 4-0-( -D-glucopyranosyl)-D-glucopyranose. It is the —OH group on C-4 that serves as the alcohol in the glucoside formation both halves of the molecule contain the six-membered, pyranose ring. 

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. 

BI< Tang, W Kalow. Amobarbital metabolism in man N-glucoside formation. Res Comm Chem Pathol Pharmacol 21 45—53, 1978. 

---