Ruff degradation is a reaction used to shorten the open chain forms of monosaccharides. It is functionally the reverse reaction of Kiliani-Fischer synthesis. In 1898, Otto Ruff published his work on the transformation of D- Glucose to D-

Arabinose Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally ...

later called the Ruff degradation. In this reaction, D-Glucose is converted to D-Arabinose. In this reaction, the terminal aldehyde group is converted to a

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

group, using selective oxidation of the aldehyde using

Bromine water Bromine water is an oxidizing, intense brown mixture containing diatomic bromine (Br2) dissolved in water (H2O). It is often used as a reactive in chemical assays of recognition for substances which react with bromine in an aqueous environment wi ...

and then converted to gluconate ion. Next, Fe(OAc)₃ with 30% of H₂O₂ is added. Thus COO- ion will form and a stereo selective compound will form. And below -CH2OH will convert to -CHO group through the reduction of iron from its +3 state to +2 state, thus forming D-Arabinose. RuffDegradation

This reaction was an important tool used by Emil Fischer to show that D-Glucose and D-Mannose each formed the same product upon Ruff degradation (D-Arabinose) indicating them to have opposite configurations at C-2 (epimers). Further Ruff degradation on D-Arabinose gave D- Glyceraldehyde, which established the stereochemistry of the chiral center on C-5.

References

Name reactions Degradation reactions {{Reaction-stub

See also

References