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In Fischer projection:
o -anomer of a D sugar has the hydroxyl group at the right of the anomeric carbon
o -anomer of a D sugar has the hydroxyl group at the left of the anomeric carbon
Mutarotation: Free carbonyl species can readily form an - or -anomer, can be converted from one form to
another
Only one anomer of -D-ribose (RNA) & -D-deoxyribose exists (DNA)
Hayworth projection formulas: cyclic structures of sugars, planar 5- or 6-membered rings, represent
stereochemistry of sugars
Furanose: 5-membered ring, planar
Pyranose: 6-membered ring, chair conformation
Fischer
Hayworth
o D sugars, right down; left up
Terminal (-CH2OH) is found on the carbon atom with the highest number in the numbering scheme
If the end residue is a free hemiacetal, it will test positive as a reducing sugar
Biochemical Connections: Vitamin C is related to sugars
Vitamin C (ascorbic acid): unsaturated lactone with a 5-membered ring
Each C is bonded to an OH except for the carboxyl group involved with the cyclic ester bond
Air oxidation of Vit. C
hydrolysis of ester bond: loss of activity as a vitamin
Vitamin C deficiency
scurvy
Scurvy: defects in collagen structure cause skin lesions & fragile blood vessels
Hydroxyproline: necessary for collagen stability because of the hydrogen-bonded cross-links between collagen
strands
What are some other important derivatives of sugar?
Amino sugars: an amino group (NH2) instead of a hydroxyl group (OH) of the parent sugar
N-acetyl amino sugars: contains an acetyl group (CH3CO)
o Ex. N-acetyl--D-glucosamine & N-acetyl--D-muramic acid (has an added carboxylic chain) found in
bacterial cell walls (peptidoglycan)
16.3 Some Important Oligosaccharides
Disaccharides: 2 monosaccharides linked by a glycosidic bond
o Ex. Sucrose, Maltose, Lactose, Isomaltose, Cellobiose
What makes sucrose an important compound?
Sucrose
o Common table sugar, extracted from sugarcane & sugar beets
o -D-glucose (aldohexose, pyranose) + -D-fructose (ketohexose, furanose)
o ,(1 2)
o Non-reducing sugar; glucose & fructose are reducing sugars singly
o Hydrolyzed when consumed to provide energy
Fructose: sweeter than sucrose, smaller amount can produce same sweetness as sucrose
Saccharin: artificial sweetener, caused cancer to laboratory animals
Sucralose: Splenda, cannot be metabolized by the body, has galactose derivative, safe sugar substitute
Biochemical Connections: Fruits, Flowers, Striking Colors, and Medicinal uses too
N-glycosides: sugar binds to the nitrogenous & aromatic base as found in ATP, vitamins, DNA & RNA
Anthocyanins: sugar derivatives of red & blue colored flowers, water-soluble, polar
Cinnamaldehyde (cinnamon) & vanillin (vanilla)
Digitalis: prescribed for irregular heartbeat
Laetrile: benzaldehyde derivative with a glycosidic linkage to glucuronic acid, thought to fight cancer with
cyanide moiety
Biochemical Connections: Lactose Intolerance: Why do so many people not want to drink milk?
Sugar intolerance: inability to digest or metabolize sugars
Lactose: milk sugar
Deficiency of the enzyme lactase causes buildup of lactose in the stomach
Bacterial lactase reaction digestive problems: bloating & diarrhea
Galactosemia: if the enzyme that catalyzes a subsequent reaction in the pathway is missing, galactose builds up
Severe problem for infants, causes swelling: when brain is affected, retardation might happen
Are there any other disaccharides important to us?
Lactose
o -D-galactose + -D-glucose
o (1 4); since galactose is a C-4 epimer of glucose
o Reducing sugar
Maltose
o Obtained from the hydrolysis of starch
o 2 residues of D-glucose in an (1 4)
o Used in beverages such as beer & milk
Cellobiose
o Obtained from hydrolysis of cellulose
o 2 residues of D-glucose in a (1 4)
Major structural component of exoskeleton of invertebrates: insects & crustaceans + algae, yeast, fungi
What role do polysaccharides play in the structure of cell walls?
Heteropolysaccharides are major components of bacterial cell walls
(1
4) linkages of N-acetyl-D-glucosamine & N-acetylmuramic acid
N-acetylmuramic acid has a lactic acid side chain [OCH(CH3) COOH] on C3; found only in prokaryotic cell walls
Staphylococcus aureus has an oligomer of 4 amino acids (tetramers) which is bonded to N-acetylmuramic acid;
this is cross-linked by another 5 amino acids (pentaglysine)
Bacterial cell walls are one of the few places where D-amino acids occur in nature; this protects bacteria from
hydrolysis
Cross-linking of polysaccharides make up the peptidoglycan
Pectin: made up mostly of D-galacturonic acid, derivative of galactose
Lingnin: major non polysaccharide component in plant cell walls, polymer of coniferyl alcohol; tough & durable
material
Plant cell walls contain little peptide or protein
Do polysaccharides play any specific roles in connective tissue?
Glycosaminoglycans: polysaccharide based on a repeating disaccharide in which one of the sugars is an amino
sugar and at least one of them has a negative charge(sulfate or carboxyl group)
Heparin: natural anticoagulant, helps prevent blood clots
Hyaluronic acid: vitreous humor of the eye & lubricating fluid of joints
Chondroitin sulfates & keratin sulfate: components of connective tissue
Glucosamine sulfate & chondroitin sulfate: help repair frayed or damaged cartilage, knees
16.5 Glycoproteins
Glycoproteins: contain carbohydrate residues in addition to the polypeptide chain, involved in immune response
o Ex. Antibodies bind to and immobilize antigens
o Antigenic determinants antigenic molecule that antibodies recognize to which they bind