Biochemistry: A Short Course - MyWeb

Biochemistry: A Short Course - MyWeb

Carbohydrates: Structure and Function Sugar features 3 carbon minimum; aldehyde or ketone present; (C H2O)n Energy storage; lubricant; signaling Carbohydrate Isomeric Forms

H D-Aldose Sugar Configurations Numbering begins at the carbonyl end of the sugar Penultimate carbon

(pink) sets Lversus D-form Isomer Classification Constitutional Isomers? Enantiomers? Diastereomers? Epimers?

Anomers? What is the Enantiomer of D-Erythrose? D-Ketose Sugar Configurations Carbonyl carbon (blue) is the anomeric carbon that generates two anomeric forms in the cyclic structure

Anomeric carbon switches between an achiral and chiral form Pyanose Formation by Intramolecular Linkage Furanose Formation by Intramolecular Linkage

Numbering via anomeric-carbon identification? Fructose Isomers Anomeric Carbon Alpha hydroxyl down Beta hydroxyl up Isomer Options Constitutional or

Stereo-isomers? Enantiomers or diastereoisomers? Epimers or anomers? Carbohydrate Isomeric Forms H

Pictorial Representations of Glucose Cyclic form Haworth project and chair configuration Linear form Fisher projection Most abundant natural form? Why is only one configuration the most abundant form?

Corn Syrup and Honey Rich in Fructose Does this isomeric exactness really matter for enjoying life? Perceived as highly sweet

Perceived as mildly sweet Reducing Sugars - Reactive Aldehydes The protein modification referred to as advanced glycosylation end products (AGE) is implicated in aging, arteriosclerosis and diabetes Hemoglobin glycosylation

is a high bloodsugar marker Experiment Benedicts reagent Observation Inference

Test solution + Benedict's Red ppt or green ppt or reagent; boil & cool. yellow ppt obtained Reducing sugar e.g. Glucose is present Test solution + Benedict's

Solution remains clear reagent; boil & cool. Non-reducing sugar e.g. Sucrose is present Disaccharide Biosynthesis via Glycosyltransferase Reaction

Alpha and Beta Assignments for Anomeric Carbons Only Why is frucofuranosyl labeled in a beta configuration?

Flipping a Box Upright On Its Legs Legs up shift to down Leg left shifts to right Left peg up stays up Legs in front stay front Cellulose Straight Chains -1,4 Linkage

Plant fiberforming structural polymer Most abundant organic compound in nature Dietary fiber; not digested except by bacteria

Glycogen and Starch Bent Chain -1,4-Linkage Homopolymer for glucose storage Muscle/liver glycogen rich; 1,6 branched linkage (1 in 10) Plant tissue

with amylose (unbranched) & amylopectin (1 in 30 branching) Glycoproteins Carbohydrates Attached to Proteins More protein than

carbohydrate N-linked via Asn or O-linked via Ser or Thr Chemical signature for protein or whole cell surfaces Glycosylation of Extracellular Proteins Red blood cell stimulatory

hormone: erythropoietin (EPO) Glycosylation enhances stability Endurance athletes illegally use to increase oxygencarrying capacity EPO spiking-detection based on glycosylation patterns

Modified Saccharides N- O- C-glycosidic linkages Increase biochemical versatility (e.g. chemical signaling) Glycosaminoglycan Structural Units Chitin: N-acetylglucosamine homopolymer Present in insect, crustacean, and arachnid exoskeleton

Second most abundant polysaccharide in nature Glycosaminoglycan Heteropolymers Glucosamine/galactosamine amino sugar derivatives Repeating disaccharide units with negatively charged group

Proteoglycans Polysaccharides & Proteins Lubricants , structural components, and cell adhesion Cartilage collagen (strength) and agrecans (shock absorber) More polysaccharide than protein Chapter 11 Problems: 1, 3, 5, 7, 9, 13, 15, 17, 19, 27 and 31

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