Biomolecules Lecture-4
Glycoside formation
Carbohydrate acetals are called glycosides, and an acetal of glucose is called glucoside
Acetals of mannose are mannoside
Acetals of fructose are fructoside
Mechanism for the reaction
Glycosides are stable in basic solution
In acidic solution it gets hydrolyzed to produce, alcohol and sugar
Aglycon
Mechanism
Anomeric effect
$\beta$-D glucose is more stable then $\alpha-D$-glucose
OH group for the equatorial position is not as a large as expected
Relative amounts of $\beta$-D glucose and $\alpha$-D-glucose are $2: 1$
glucose reacts with an alcohol $\rightarrow$ glucoside
(major product is the $\alpha$-glucoside)
$\alpha$ glucoside must be more stable than the $\beta$-glucoside
The preference for certain substituents bonded to the anomeric carbon for the axial position is called the anomeric effect
Reducing and non reducing sugar
Glycosides are non-reducing sugars
Hemiacetals, on the other hand are in equilibrium with the open-chain
So they can reduce the oxidizing reagent
reducing sugar
Measuring the blood glucose levels in diabetes
Hemoglobin
Thank you