Ruff degradation

Ruff degradation is a reaction used to shorten the open chain forms of monosaccharides.^[1] 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 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 group, using selective oxidation of the aldehyde using Bromine water and then converted to gluconate ion. Next, Fe(OAc)₃ with 30% of H₂O₂ is added.

Thus COO- ion will form CO₂ 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.

Hexoses converted to pentoses by Ruff degradation

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

^ Stapley, Jonathan A.; BeMiller, James N. (2007-02-26). "The Ruff degradation: a review of previously proposed mechanisms with evidence that the reaction proceeds by a Hofer–Moest-type reaction". Carbohydrate Research. Synthesis and Structure of Glycans. 342 (3): 407–418. doi:10.1016/j.carres.2006.12.002. ISSN 0008-6215.

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[1] Stapley, Jonathan A.; BeMiller, James N. (2007-02-26). "The Ruff degradation: a review of previously proposed mechanisms with evidence that the reaction proceeds by a Hofer–Moest-type reaction". Carbohydrate Research. Synthesis and Structure of Glycans. 342 (3): 407–418. doi:10.1016/j.carres.2006.12.002. ISSN 0008-6215.

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See also

References