Question

In acidic solutions, nucleosides are hydrolyzed to a sugar and a heterocyclic base. Propose a mechanism for this reaction.

Short answer

A compound containing a base bonded to d-ribose or to 2′-deoxy-d-ribose is called a nucleoside or these are glycosylamines made by attaching a nucleobase to a ribose or deoxyribose ring.

Adenosine

Guanosine

Deoxyadenosine

Deoxyguanosine

Step-by-step solution

Step 1:Nucleoside

A compound containing a base bonded to d-ribose or to 2′-deoxy-d-ribose is called a nucleoside or these are glycosylamines made by attaching a nucleobase to a ribose or deoxyribose ring.

Adenosine

Guanosine

Deoxyadenosine

Deoxyguanosine

Mechanism for the reaction

Nucleoside undergoes hydrolysis to form sugar and base. The example is represented as follows:

Hydrolysis of nucleoside

The mechanism for the reaction is as:

Mechanism