Ribose Created 2026-10-14 Updated 2026-10-31
Ribose is a monosaccharide with molecular formula . Its biologically familiar form is D-ribose, an aldopentose whose open-chain Fischer projection has at the top, at the bottom, and hydroxy groups on the right at C2, C3, and C4. The opposite horizontal substituents are hydrogen. See McMurry, Organic Chemistry, 25.3: D-ribose and D-glucose configurations.
Figure 1.
Open-chain Fischer projections of D-ribose and 2-deoxy-D-ribose
. At each cross, horizontal chemical bonds point toward the viewer and vertical chemical bonds point away. Both drawings number the free sugar from its aldehyde carbon, C1. In deoxyribose, C2 has two hydrogen substituents and is not a stereocenter. These are open-chain reference structures, not a depiction of the predominant chemical species in water. Details.
Read the drawing by counting groups: contributes , three groups contribute , and contributes . Their sum is . The count checks composition; the right/right/right pattern additionally specifies the stereochemistry of D-ribose.
In RNA, ribose occurs as a ring within each nucleotide, joining a nucleobase to the phosphate-linked backbone. Its C2 position retains a hydroxy group, unlike deoxyribose in DNA. In a nucleotide, the sugar positions carry primes, so this is C2′. See Alberts et al.: nucleotide sugars in RNA and DNA. Free ribose in water is also predominantly cyclic, with several ring forms in chemical equilibrium and very little open-chain form; the Fischer projection is valuable for comparing configurations, not for estimating their abundances. See Mason et al., The Conformation of a Ribose Derivative in Aqueous Solution: A Neutron Scattering and Molecular Dynamics Study (2013), introduction.
Sanger sequencing Created 2026-10-18 Updated 2026-10-20
Sanger sequencing determines a DNA nucleotide sequence by extending a common sequencing primer and occasionally incorporating a dideoxynucleoside triphosphate. A normal deoxynucleoside triphosphate already has hydrogen in place of a hydroxy group; it retains the hydroxy group. A dideoxynucleoside triphosphate lacks that hydroxy group too. It can join the growing strand because the preceding nucleotide supplies the reacting hydroxy group. Once incorporated, its own end cannot form the next phosphodiester bond. Thus the blocked step is the next addition, not attachment of the terminator itself.[ref]
Figure 1.
A dNTP retains a hydroxy group; a ddNTP permits incorporation but blocks the next extension
. Original chemical-feature and chain-extension schematic. Both substrates have -H; only the dNTP has -OH. Boxes omit most chemical atoms and do not specify stereochemistry. The lower rows show incorporated units, which no longer carry the substrate's complete triphosphate group. The previous strand end attaches either substrate; the difference appears at the new terminal end. This is a conceptual drawing, not molecular imaging or experimental data. Details.
In the historical four-reaction format, each tube receives copies of the same template, the same sequencing primer, a DNA polymerase and all four ordinary deoxynucleoside triphosphates. The tubes differ in their terminating substrate: ddATP, ddCTP, ddGTP or ddTTP. In the A reaction, ordinary dATP can allow copying to continue past one A position, whereas incorporation of ddATP stops another copy there. Competition produces a family of endpoints, rather than every strand stopping at the first A. Adjusting substrate proportions makes later endpoints detectable. A lane identifies the terminating nucleobase in the new strand, not the complementary template letter.[ref]
The readout requires gel electrophoresis capable of separating single-stranded DNA fragments differing by one nucleotide. Historical denaturing polyacrylamide gel electrophoresis suppressed strand folding and resolved these adjacent lengths; radioactive labels were detected by autoradiography. An ordinary agarose gel electrophoresis comparison with a 100-base pair DNA ladder does not supply that resolution. Four separate reaction lanes carry the identities in this format.[ref]