Examines the structure of sugars, from simple monosaccharides to complex energy-storage polymers.
Why can you easily digest a starchy potato but not a piece of wood, even though both are made entirely of the same glucose building blocks?
Carbohydrates are polyhydroxy aldehydes or ketones with the general formula . We classify them by their functional groups: aldoses contain an aldehyde at , while ketoses contain a ketone at . In aqueous solutions, these linear chains spontaneously close into rings. This cyclization creates a new chiral center at the anomeric carbon ( for glucose). If the hydroxyl group () at points down, it is the **-anomer; if it points up, it is the -anomer**. This tiny spatial difference determines whether the resulting polymer is a soft energy source or a rigid structural material.
Quick Check
If a hexose sugar has a carbonyl group at the second carbon in its linear form, is it an aldose or a ketose?
Answer
It is a ketose.
When two monosaccharides join, they undergo a dehydration synthesis reaction. A hydroxyl group from one sugar reacts with the anomeric carbon of another, releasing a molecule of and forming a glycosidic bond. The notation for these bonds is critical. For example, an linkage means the on was in the position and connected to the of the next sugar. These bonds can create long linear chains or highly branched networks depending on which carbons are involved.
1. Take two molecules of -D-glucose. 2. Align of the first molecule with of the second. 3. Remove from and from the hydroxyl group. 4. The resulting glycosidic bond creates the disaccharide maltose.
Polysaccharides serve two main purposes: energy storage and structural support. Starch (in plants) and glycogen (in animals) use linkages, which cause the chains to twist into a helical shape, making them compact and easy for enzymes to break down. Starch consists of amylose (unbranched) and amylopectin (branched via bonds). Cellulose, however, uses linkages. This causes the chains to remain straight, allowing them to pack tightly and form hydrogen bonds between adjacent chains, creating the immense tensile strength found in plant cell walls.
Compare the branching of Amylopectin and Glycogen: 1. Amylopectin has branches roughly every 24–30 glucose units. 2. Glycogen is much more highly branched, with points every 8–12 units. 3. Result: Glycogen can be mobilized (broken down into glucose) much faster than starch because more 'ends' are available for enzymatic attack.
Quick Check
Why can humans digest starch but not cellulose?
Answer
Human enzymes (like amylase) can only hydrolyze linkages; they lack the specific shape to break linkages found in cellulose.
Identify the bond in a polymer where the glucose units are 'flipped' 180 degrees relative to each other. 1. Observe the orientation of the glycosidic oxygen. 2. If the units alternate orientation, it indicates a linkage. 3. This structure allows for inter-chain hydrogen bonding, characteristic of cellulose.
Which carbon atom becomes the 'anomeric carbon' during the cyclization of glucose?
What type of bond is responsible for the branching seen in amylopectin and glycogen?
Cellulose is a polymer of -D-glucose.
Review Tomorrow
In 24 hours, try to sketch the difference between an and a glycosidic bond from memory.
Practice Activity
Look at a nutrition label for 'Fiber' and 'Total Carbohydrates.' Based on today's lesson, which parts of that label represent -linkages vs -linkages?