How do you identify alpha and beta forms in sugars?

1 Answer
Jul 22, 2015

You look at the position of the "OH" (or "OR") group at the anomeric carbon.

Explanation:

The cyclic forms of carbohydrates can exist in α and β forms, based on the position of the substituent at the anomeric carbon.

To assign the α or β configuration to the cyclic form of a carbohydrate, look at the relative positions of the "CH"_2"OH" group and the "OH" (or "OR") group at the anomeric carbon.

Alpha Beta Glucose
(from chemistry2.csudh.edu)

If you consider the 6-membered ring to be flat, the exocyclic "O" atom at the anomeric carbon is on the "bottom" side of the ring, and the "CH"_2"OH" group is on the "top" side of the ring.

The "CH"_2"OH" group and the anomeric #"OH" group are on opposite sides of the ring.

In the β- form, the exocyclic "O" atom at the anomeric carbon is on the same side of the ring as the "CH"_2"OH" group.

Lactose is a disaccharide that consists of galactose and glucose units.

studydroid.com
(from www.studydroid.com)

Its systematic name is β-D-galactopyranosyl-(1→4)-D-glucose.

That tells you that the "O" atom on "C-1" of the galactose is β (on the same side as the "CH"_2"OH" group) and joined in a glycoside linkage to "C-4 "of the glucose unit..

If the glucose unit has the anomeric "OH" group in the α position, we have α-lactose.

If the glucose unit has the anomeric "OH" group in the β position, we have β-lactose.