Carbohydrates: Sugars, 9

Chapter
Saccharides, Glycans

Figure.

Table.

Tools of Biochemistry 9A:

SEQUENCING OLIGOSACCHARIDES

1
 Aldoses and Ketoses 醛糖與酮糖

• An aldose contains an aldehyde functionality

• A ketose contains a ketone functionality
Horizontal bonds are pointing toward you;
vertical bonds are projecting away from you.
 Enantiomers 鏡像異構物

• Enantiomers
– Stereoisomers that are nonsuperimposable mirror images
• In sugars that contain many chiral centers, only the one
that is most distant from the carbonyl carbon is
designated as D (right) or L (left)
• D and L isomers of a sugar are enantiomers
– For example, L and D glucose have the same water solubility
• Most hexoses in living organisms are D stereoisomers
• Some simple sugars occur in the L-form, such as L-
arabinose
 Diastereomers 非鏡像異構物

• Diastereomers: stereoisomers that are not mirror images

• Diastereomers have different physical properties
– For example, water solubilities of threose and erythrose are
different

1. Enantiomer
Isomer
同分異構物 2. Diastereormer
Hemiacetals and Hemiketals 半縮醛與半縮酮

• Aldehyde and ketone carbons are electrophilic

• Alcohol oxygen atom is nucleophilic
• When aldehydes are attacked by alcohols, hemiacetals form
• When ketones are attacked by alcohols, hemiketals form
Cyclization of Glucose & Fructose
α & β Anomers Can Interconvert
N-Glycosides

糖苷鍵結
Formation of O-Glycosides
Figure 2-19 Molecular Biology of the Cell (© Garland Science 2008)
Figure 2-20 Molecular Biology of the Cell (© Garland Science 2008)
 Glycoconjugates: Glycoprotein
• A protein with small oligosaccharides attached
– Carbohydrate attached via its anomeric carbon
– About half of mammalian proteins are glycoproteins
– Carbohydrates play role in protein-protein recognition
– Only some bacteria glycosylate few of their proteins
– Viral proteins heavily glycosylated; helps evade the immune
system
 Oligosaccharides are
Conformationally Mobile