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These protecting groups “lock” the sugars into a rigid chair conformation. When the sugar forms the necessary oxocarbenium ion, it flattens at the anomeric position. This change in configuration is a high-energy transformation when cyclic protecting groups are present, and leads to the sugar being “disarmed”. [3]
Ethylene glycol protects a ketone (as an acetal) during an ester reduction, vs. unprotected reduction to a diol. A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction.
However, in order for anomers to exist, the sugar must be in its cyclic form, since in open-chain form, the anomeric carbon atom is planar and thus achiral. More formally stated, then, an anomer is an epimer at the hemiacetal/hemiketal carbon atom in a cyclic saccharide. [1] Anomerization is the process of conversion of one anomer to the other.
The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form—due to the presence of alcohol and aldehyde or ketone functional groups, the form having the straight chain can easily convert into a chair-like hemiacetal ring structure commonly found in carbohydrates.
The rotation of the solution will increase from +18.7° to an equilibrium value of +52.7° as some of the β form is converted to the α form. The equilibrium mixture is about 64% of β- D -glucopyranose and about 36% of α- D -glucopyranose, though there are also traces of the other forms including furanoses and open chained form.
Structure of the benzylidene acetal of glucose. In organic chemistry , a benzylidene acetal is the functional group with the structural formula C 6 H 5 CH(OR) 2 (R = alkyl, aryl). Benzylidene acetals are used as protecting groups in glycochemistry.
Hemiacetals form in the reaction between alcohols and aldehydes or ketones. Using an acid catalyst, the reaction proceeds via nucleophilic attack of the carbonyl group by the alcohol. [4] A subsequent nucleophilic attack of the hemiacetal by the alcohol results in an acetal. [2] Solutions of simple aldehydes in alcohols mainly consist of the ...
If the glycone group of a glycoside is glucose, then the molecule is a glucoside; if it is fructose, then the molecule is a fructoside; if it is glucuronic acid, then the molecule is a glucuronide; etc. In the body, toxic substances are often bonded to glucuronic acid to increase their water solubility; the resulting glucuronides are then excreted.