Day 1 Carbs, Lipids, and Proteins Flashcards
Carbohydrate Components
- Consist of polyhydoaldehydes and ketones
- the structures are monosacharides (simple 3-7 carbon of sugar), dissacharides (2 sugar linked in a glycosidic bond), or polysaccharide (complex carbs with many monoS.)
Aldohexoses
- They have 4 chiral center and eight different configurations that can exist in 3 forms (alpha, beta or linear)
- D configuration on the highest chiral carbon are found in all living systems
Ketoses
- the carbonyl center is almost always on C2
there are 4 configurations that exist in 5 different forms (alpha, beta, linear, furanose, or pyranose)
Dissacharides
Some common dissacharides are sucrose, maltose and lactose.
Polysaccharides
- Can be linear or branched
- Some common ones are cellulose (linear beta 1-4 linked glucose), amylose (linear alpha 1-4 linked glucose), amylopectin and glycogen (linear alpha 1-4 linked glucose with alpha 1-6 branches)
Fisher projections
- horizontal bonds are towards me and the vertical bonds are away from me.
- designated L or D based on the position of the OH on the last chiral center away from the carbonyl
- L is left and D is right
Reactions of monosaccharides
ketoses and aldoses can cyclize to form an intramolecular hemiacetal bond (oh attacks carbonyl) that will result in a hexoses and/or ketopentoses
Anomeric Carbon
Carbonyl carbon that was not a stereocenter while in the linear form becomes a stereoactive center in the ring form. It designates alpha and beta status .
Mutarotation
Linear form, alpha ring and beta rings will exist together in equilibrium.
Cyclization
- Aldoses can form a pyranose ring which is when the OH on C6 attacks the carbonyl group and form a 6 membered ring.
- Ketoses can form a pyranose ring or a furanose ring which is when the OH on C5 attacks the Carbonyl group.
Haworth Projection (forming the ring)
- Cyclic O is placed at 1-oclock with anomeric C on its right
- designate if the sugar is L or D. If it is L then the CH2OH of carbon 6 is below the plane consequently if the sugar is D then place it above the plane
- groups of OH on the right side of the carbon chain are placed below the ring while groups of OH on the left side of the carbon chain are placed above the ring.
Haworth Projection (naming the ring)
- alpha will be assigned to the anomeric carbon if the OH group is trans to the CH2OH group.
- beta will be assigned to the anomeric carbon if the OH group is cis to the CH2OH group.
Glycosidic bonds
- Linking two sugars together the via a hydroxyl bond (O glycosidc) or via an amine (N glycosidic).
- U shaped bonds indicate that the sugar on the left was in alpha position.
- Z shaped bonds indicate that the sugar on the left was in beta position.
Nonreducing ends
the anomeric C is involved in the glycosidic bond
Reducing end
The anomeric C is free and can easily convert back to its linear shape.