Γ-Amino-Boronic ACIDS MEDIATED PASSIVE TRANSPORT OF GLYCOPYRANOSIDES THROUGH a LIQUID ORGANIC MEMBRANE

Abstract

The ability of γ-amino-propylboronic acids to transport phenyl ß-D-glucopyranoside and phenyl ß-D-galactopyranoside through a liquid organic membrane in the presence of trioctylmethylammonuim chloride was determined. Under the conditions examined, glycoside transport was facilitated by the reversible formation of covalent tetrahedral, anionic glycosideboronate complexes, which partitioned into the organic membrane as lipophilic ion pairs. The apparent order of glycoside selectivity for the tetrahedral boronate transport was to be cis α,γ-diol> α,β-diol. The results indicate that the N->B intramolecular dative bond and the Hydrophile-Lipophile-Balance (HLB) of the formed complex influence the glycoside transport rate.

1,3‐Dihydro‐1‐hydroxy‐3‐morpholin‐4‐yl‐2,1‐benzoxaborole: product of the reaction of o‐formylphenylboronic acid with morpholine

“…1 Aminoboronic acids are also able to transport sugar molecules through liquid organic membranes. 2 From the point of view of their applications, the structures of these compounds have been investigated widely both in the solid state and in different solutions. The presence of a nitrogen atom gives the possibility of the formation of an intramolecular N-B bond, which enables complexation of the sugars at neutral pH.…”

Synthesis of C–B–O five membered ring by hydroboration of allylalcohols in standard conditions

“…The organoboron compounds are known for their great interest in chemical synthesis (Steinberg and Brotherton, 1966;Brown and Unni, 1968;Brown, 1975), in asymmetric synthesis (Corey et al, 1997;Corey and Rodhes, 1997;Abiko et al, 1997;Niatteson and Majumdar, 1980), in cancer therapy as ''cluster of boron'' (Hatanaka and Nakagawa, 1994), Barth et al, 1992) in biology (Dugger, 1983;Hu and Brown, 1994), in transport of sugars as catalyst transfer agent (Dicko et al, 2001). Certain organoboron compounds have an interest in the formulation of some lubricants because of their antioxidize properties (Guanqui et al, 2000).…”