deoxyribofuranose

Deoxyribofuranose, also called 2'-deoxyribose, is a five-carbon sugar in the furanose form that constitutes the backbone of DNA. Its molecular formula is C5H10O4. In contrast to ribose, the sugar found in RNA, deoxyribose lacks a hydroxyl group at the 2' position, a feature that contributes to the chemical stability of DNA and influences the geometry of the sugar-phosphate backbone.

In nucleotides, deoxyribose cyclizes to a five-membered ring in which the anomeric carbon (C1') bears the attached nitrogenous base via a glycosidic bond. The molecule is chiral and biologically occurs in the D-configuration, with the ring able to adopt alpha or beta anomers. In DNA, the sugar typically adopts a C2'-endo (south) pucker, which relates to the B-form geometry, whereas RNA uses ribose with a C3'-endo conformation.

Deoxyribose is produced in cells by the reduction of ribonucleotides through the action of ribonucleotide reductase, providing deoxyribonucleotides for DNA synthesis. The absence of the 2'-hydroxyl group reduces susceptibility to hydrolysis and nuclease attack, contributing to DNA’s stability. The sugar’s configuration governs the phosphodiester linkage between adjacent nucleotides, linking the 3' carbon of one sugar to the 5' carbon of the next via phosphate groups. Deoxyribose thus underpins the structure and properties of DNA.