Chapter11-MyWeb.pptVIP

* * * * * * * * * * * * * * * * * 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 L- versus 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 Perceived as highly sweet ? Perceived as mildly sweet Does this isomeric exactness really matter for enjoying life? Experiment Observation Inference Test solution + Benedicts reagent; boil cool. Red ppt or green ppt or yellow ppt obtained Reducing sugar e.g. Glucose is present Test solution + Benedicts reagent; boil cool. Solution remains clear Non-reducing sugar e.g. Sucrose is present 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 blood- sugar marker Benedict’s reagent Disaccharide Biosynthesis via Glycosyltransferase Reaction Alpha and Beta Ass