(a) Simple aminoacetals hydrolyze quickly and easily in dilute acid. Propose a mechanism for hydrolysis of the following aminoacetal:
(b) The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.
(c) The stability of our genetic code depends on the stability of DNA. We are fortunate that the aminoacetal linkages of DNA are not easily cleaved. Show why your mechanism for part (a) does not work so well with deoxycytidine and deoxyadenosine.
Solution 68SPThe oxygen is protonated by hydronium ion to form oxonium ion. The ring opening is takes place by attack of nucleophile.
(b) Ketones and aldehyde react with water to form hydrates; they also react with alcohols to form acetals. In the nucleosides, the carbon is bonded to oxygen and nitrogen this carbon is known aminoacetal carbon and this linkage this aminoacetal linkage.
The aminoacetal linkages in deoxycytidine...