Nucleic Acids - An Introduction

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The first isolation of what we now refer to as DNA was accomplished by Johann Friedrich Miescher circa 1870. He reported finding a weakly acidic substance of unknown function in the nuclei of human white blood cells, and named this material "nuclein". A few years later, Miescher separated nuclein into protein and nucleic acid components. In the 1920's nucleic acids were found to be major components of chromosomes, small gene-carrying bodies in the nuclei of complex cells. Elemental analysis of nucleic acids showed the presence of phosphorus, in addition to the usual C, H, N & O. Unlike proteins, nucleic acids contained no sulfur. Complete hydrolysis of chromosomal nucleic acids gave inorganic phosphate, 2-deoxyribose (a previously unknown sugar) and four different heterocyclic bases (shown in the following diagram). To reflect the unusual sugar component, chromosomal nucleic acids are called deoxyribonucleic acids, abbreviated DNA. Analogous nucleic acids in which the sugar component is ribose are termed ribonucleic acids, abbreviated RNA.

The acidic character of the nucleic acids was attributed to the phosphoric acid moiety.

The two monocyclic bases shown here are classified as pyrimidines, and the two bicyclic bases are purines. Each has at least one N-H site at which an organic substituent may be attached. They are all polyfunctional bases, and may exist in tautomeric forms.

Base-catalyzed hydrolysis of DNA gave four nucleoside products, which proved to be N-glycosides of 2'-deoxyribose combined with the heterocyclic amines. Structures and names for these nucleosides will be displayed above by clicking on the heterocyclic base diagram. The base components are colored green, and the sugar is black. As noted in the 2'-deoxycytidine structure on the left, the numbering of the sugar carbons makes use of primed numbers to distinguish them from the heterocyclic base sites. The corresponding N-glycosides of the...