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1,5-anhydro-2-deoxy-3-O-(2-deoxy-beta-D-arabino-hexopyranosyl)-D-arabino-hex-1-enitol, the by-product in the enzymic hydration of D-glucal by beta-D-glucosidase from emulsin. 1977

J Lehmann, and E Schröter

The by-product (3) in the hydration of D-glucal (1) catalyzed by emulsin beta-D-glucosidase has been identified as 1,5-anhydro-2-deoxy-3-O-(2-deoxy-beta-D-arabino-hexopyranosyl)-D-arabino-hex-1-enitol. Two models for the formation of 3 are discussed, involving transfer of a 2-deoxy-D-arabino-hexopyranosyl cation to HO-3 of D-glucal (glycon transfer) and transfer of an allylic D-pseudoglucal cation to HO-1 of 2-deoxy-D-arabino-hexopyranose (aglycan transfer). The enzymic production of 3 is highly regiospecific, which lends support to the second model and implies the presence of a specific binding-site for the aglycon moiety.

UI MeSH Term Description Entries
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D005959 Glucosidases Enzymes that hydrolyze O-glucosyl-compounds. (Enzyme Nomenclature, 1992) EC 3.2.1.-. Glucosidase
D006601 Hexoses MONOSACCHARIDES whose molecules contain six carbon atoms, such as GLUCOSE and FRUCTOSE. They generally have the chemical formula C6H12O6. Hexose
D001617 beta-Glucosidase An exocellulase with specificity for a variety of beta-D-glycoside substrates. It catalyzes the hydrolysis of terminal non-reducing residues in beta-D-glucosides with release of GLUCOSE. Cellobiases,Amygdalase,Cellobiase,Emulsion beta-D-Glucosidase,Gentiobiase,Emulsion beta D Glucosidase,beta Glucosidase,beta-D-Glucosidase, Emulsion
D001665 Binding Sites The parts of a macromolecule that directly participate in its specific combination with another molecule. Combining Site,Binding Site,Combining Sites,Site, Binding,Site, Combining,Sites, Binding,Sites, Combining

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