Acylation of cystosine by ethyl N-hydroxycarbamate and its acyl derivatives and the binding of these agents to nucleic acids and proteins

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690001860

Abstract

Ethyl N-hydroxycarbamte and several of its acyl derivatives specifically acylated the primary amino-group of cytosines; no reaction occurred at other sites or with the other nucleic acid bases. Compared with cytosine, the N(4)-acylcytosines showed (a) a bathochromic shift in u.v. absorption and (b) an increase in the polarity of the carbon–nitrogen bond resulting in greater ease of hydrolysis into uracils.[1-3H]Ethyl N-aacetoxy-N-acetylcarbamate with DNA, followed by enzymatic hydrolysis of the nucleic acid, produced 2′-deoxyuridine and 2′(5′)-deoxyuridylic acid. Ethyl carbamate and acetylcarbamate, and several other acyl derivatives of amonia, hydrazine, and hydroxylamine did not react with cytosine.

Recommended Literature