Write equations for the steps involved in hydrolysis of adenine deoxyribonucleoside to deoxyribose and adenine. Would you expect the reaction to occur more readily in acidic or basic solution?

The hydrolysis of adenine deoxyribonucleoside (AD) can be written as follows: \[ AD + H_2O \rightarrow Adenine + Deoxyribose \] Adenine deoxyribonucleoside is composed of the nitrogenous base adenine and the sugar deoxyribose linked by an N-glycosidic bond. The reaction consists of breaking the N-glycosidic bond by introducing a water molecule.

When it comes to hydrolysis reactions, the presence of acidic or basic solutions can affect their rate and mechanism. In acidic solution, protonation might occur in the nucleobase, making the glycosidic bond more susceptible to cleavage, leading to the formation of the adenine and deoxyribose. The reaction can be written as: \[ AD + H^+ + H_2O \rightarrow Adenine + Deoxyribose + H^+ \] In a basic solution, the hydroxide ion (OH-) attacks the electrophilic center of the glycosidic bond and makes it more prone to breakage. The reaction can be written as: \[ AD + OH^- \rightarrow Adenine + Deoxyribose + OH^- \] Considering the nature of nucleobases and their nucleophilic centers (lone pair electrons in the nitrogen atoms), the hydrolysis of adenine deoxyribonucleoside is expected to occur more readily in acidic than in basic solutions. The protonation of the nitrogen atoms in the nucleobase under acidic conditions enhances the cleavage of the N-glycosidic bond, while in a basic solution, a competition between the nucleophilic centers and the dissociation of the unshared electron pair in the nitrogen might affect the hydrolysis rate.