Weerman degradation
Encyclopedia
The Weerman degradation is an organic reaction
in carbohydrate chemistry
in which an aldonamide (derived from an aldonic acid
) is degraded by sodium hypochlorite, forming a new sugar with one less carbon. The reaction is named after R.A. Weerman
The reaction mechanism
is that of the related Hofmann degradation. One study demonstrated the direct oxidation of glucose
to arabinose
by the same sodium hypochlorite, skipping the aldonic acid and aldoamide steps.
Organic reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...
in carbohydrate chemistry
Carbohydrate chemistry
Carbohydrate chemistry is a subdiscipline of chemistry primarily concerned with the synthesis, structure, and function of carbohydrate structures. Due to the general structure of carbohydrates, their synthesis is often preoccupied with the selective formation of glycosidic linkages and the...
in which an aldonamide (derived from an aldonic acid
Aldonic acid
An aldonic acid is any of a family of sugar acids obtained by oxidation of the aldehyde functional group of an aldose to form a carboxylic acid functional group. Thus, their general chemical formula is HOOC-n-CH2OH...
) is degraded by sodium hypochlorite, forming a new sugar with one less carbon. The reaction is named after R.A. Weerman
The reaction mechanism
Reaction mechanism
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs.Although only the net chemical change is directly observable for most chemical reactions, experiments can often be designed that suggest the possible sequence of steps in...
is that of the related Hofmann degradation. One study demonstrated the direct oxidation of glucose
Glucose
Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...
to arabinose
Arabinose
Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde functional group.For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde.For sugars, the D/L...
by the same sodium hypochlorite, skipping the aldonic acid and aldoamide steps.
See also
- Curtius rearrangementCurtius rearrangementThe Curtius rearrangement , as first defined by Theodor Curtius, is a chemical reaction that involves the rearrangement of an acyl azide to an isocyanate. Several reviews have been published....
- Hofmann degradation
- Ruff-Fenton degradation
- Wohl degradationWohl degradationThe Wohl degradation in carbohydrate chemistry is a chain contraction method for aldoses. The classic example is the conversion of glucose to arabinose as shown below. The reaction is named after the chemist Alfred Wohl....