BIOCHEM LEC – CARBOHYDRATES • D- and L-Configurations

• Based on the chirality of the penultimate C

Carbohydrates • Enantiomers - pair of molecules that exist in
• "Hydrates of carbon, also called two forms that are mirror images of one
"saccharides" another but cannot be superimposed one upon
• Monosaccharides one unit the other
• Di-, tri-, etc.: 2 units
- Larger polymers:
polysaccharides
• Can be modified with other groups to
contain N. P, etc.
• General formula: (CH,O) n ≥3
• Simplest have 3 carbons

Classifying Carbohydrates

By functional group Enantiomers

• Aldose aldehyde • Enantiomers have identical physical properties
• Ketose ketone (mp, bp, etc)

• Can only distinguish them by:

- Interactions with other chiral substances

• Rotation of plane-polarized light

• Most naturally-occurring sugars are the D

enantiomer

Epimers
Classifying Carbohydrates
• Carbohydrates that differ in configuration
By number of C atoms
around only 1C other than the enantiomeric
• Triose = 3C one
• Diastereomers
• Tetrose = 4C
Cyclization
• Pentosa = 5C
• Cyclical sugars are non-planer
• Hexose = 6C

Chirality

• Chiral carbon→ Catom surrounded by

• four different groups
• Several chiral carbons in carbohydrates
• D- and L- conformations are determined by the
chirality of the penultimate carbon
• Chirality at the other carbons determines
identity
Cyclization of Glucose

• Since the aldehyde group has rotational

freedom about the C1-C2 bond, anomers are
possible
• B-D-Glucose is most prevalent in biochemistry
• More stable conformation

Cyclization

• The anomeric carbon is always bound to 2 O

atoms
• 5-membered ring-furanose
• 6-membered ring-pyranose

Reducing sugars

• any sugar that is capable of acting as a

reducing agent:
• due to the presence of reducing aldehyde or
ketone groups

Non-Reducing Sugars

• Sucrose
• Disaccharide of glucose and fructose
• Anomeric C occupied in the bond