General Index
Monosaccharide Derivatives
Index
Oxidation derivatives
If the oxidation takes place at carbon 1, the derivatives are called Aldonic Acids. In the case of D-Glucose, we get
That appears as gluconate. In the Fischer projection,
Aldonic acids can form intramolecular esters or Lactones. In the case of
Gluconic acid, an ester between carbons 1 and 5 gives
In the Haworth perspective,
Among these derivatives we can consider Ascorbic Acid:
Also known as Vitamin C. Its structure is:
When the oxidation takes place at carbon 6, the derivatives are called Uronic Acids.
In the case of D-Glucose, we get D-Glucuronic Acid:
A relevant biomolecule in Detoxification processes:
The C6-epimer of Glucuronic acid is
Both acids enter in the composition of Glycosaminoglycans. The structure of Iduronic Acid is:
Reduction Derivatives
Carbonyl groups in aldoses or ketoses can be reduced and the resulting compound is a polyalcohol. In the case of
D-Glucose, the polyalcohol is
In Fischer projection, its structure is
The result of the reduction of D-Mannose is
In the Fischer projection, the structure of Mannitol is:
Reduction of trioses (Glyceraldehyde or Glycerone) we obtain
Having no asymmetrical carbons, we adopt the sn convention. If we place the molecule with carbon 2 in the same
configuration as L-Glyceraldehyde, carbon sn-1 is up and carbon sn-3 is down. Carbon sn-2 is the secondary alcohol. In Fischer projection formula,
Deoxysugars
When we substitute a hydroxyl group -OH in a monosaccharide by an hydrogen -H, the resulting compounds are Deoxysugars.
An important one is the 2-deoxy derivative of D-Ribose,
that forms part of Deoxynucleotides, the monomers of DNA (Deoxyribonucleic Acid). Its structure is
Other deoxyderivatives are
Or 6-deoxy-L-Mannose:
And also
Or 6-deoxy-L-galactose. Its structure is:
Both appear in complex oligo- and polysaccharides.
Aminosugars
Aminoderivatives arise when we substitute a hydroxyl -OH group by an amino -NH2. This group normally appears acetylated. This is the case of
Whose structure is:
As well as
Its structure being
They appear in complex oligo- and polysaccharides.
An important aminoderivative is
also known as N-Acetyl Neuraminic Acid (NANA). It appears in complex oligosaccharides and glycoconjugates (Glycolipids, Glycoproteins). its structure is
Phosphoric Esters
The metabolically-active forms of sugars are phosphoric esters. Thus, D-Glucose forms
Its structure is:
Other form is the hemiacetal phosphate
Its structure being
D-Fructose also forms phosphoric esters. For instance,
Whose structural formula is:
Also the bisphosphate
In Haworth perspective is:
Other interesting phosphoric ester is
its structure is:
It is a key intermediate in the dark phase of Photosynthesis.