Bio 98 - Lecture 11

Carbohydrates

a.k.a. Sugars…

I. Definition of a carbohydrate
General formula: (CH2O)n , ―hydrated carbon‖ Example: C6H12O6 is glucose Many carbohydrates have more complex formulas & contain amino, phosphate, sulfate & other groups

II. Functions

1. Fundamental source of metabolic energy for most life forms.
2. Components of many important biomolecules.

plants respiration carbohydrate + O2 ATP ADP .1. Carbohydrates as an energy source sunlight plants photosynthesis CO2 + H2O animals.

glycolipids . fructose. plant fiber.etc.deoxyribose and ribose Carbohydrates are often polymers Monosaccharides: glucose.wood. starch) . Oligosaccharides: di-. tri-.cell membranes DNA. etc. Biological molecules Penicillin Cellulose .e.exoskeleton of arthropods Cell walls of bacteria & yeast Glycoproteins. RNA . etc. Chitin . tetra. ribose.2. Sucrose is a disaccharide: glucose + fructose Polysaccharides: can be linear or branched (i.

. .. pentose.. . octose 2.Monosaccharide nomenclature 1. hexose. Carbon number: triose.. Aldoses and ketoses C# 1 2 3 4 5 6 D-glucose D-fructose HC=O HC-OH HO-CH HC-OH H2C-OH C=O HO-CH HC-OH HC-OH H2C-OH HC-OH H2C-OH an aldohexose a ketohexose .

How many chiral carbons are in glucose? . compare mannose.Asymmetric (chiral) carbons allow many distinct monosaccharides. which are all aldohexoses. and galactose. glucose.

identical structures except for configuration (chirality) at one or more carbons.).g. Glucose and galactose are epimers at carbon 4. 2. however (1. half of these represent enantiomers (3.). designated as D.O-chem terms relevant to monosaccharide structure 1. all aldohexoses are diastereomers of each other. Number of unique names = 24 / 2 = 8. diastereomers . enantiomers . 3. . How many aldohexose names are possible? 2 configuration choices at each of 4 asymmetric carbons.mirror images.differ in chirality at only one carbon. e.& L-.. does not constitute a name change. epimers .

+ HC=O HC-OH 5-member ring: furanose 6-member ring: pyranose When forming a ring. giving rise to 2 possible anomers. HO-CH HC-OH ..Ring structures Most pentoses and hexoses spontaneously form ring (cyclized) structures in solution. a new asymmetric center is created. HC-OH H2C-OH Dglucose(linear form) .

Linear form Haworth projection hemiacetal a and b anomers a-D-glucopyranose .

In solution rapid mutarotation occurs b-D-glucopyranose (~66%) Linear D-glucose (1%) a-D-glucopyranose (~33%) .

wheat 3. 2 monosaccharides joined covalently by an O-glycosidic bond .malted (germinating) barley.milk sugar • maltose . Three common disaccharides • sucrose . Mainly found in plants 2.sugar cane.Disaccharides 1. sugar beets • lactose .

Formation of hemiacetal and acetals Glycosidic bond .

Common disaccharides are produced by enzymecatalyzed condensation/dehydration reactions Can be either a or b due to mutarotation .

Notice: there is no hemiacetal .

plant fiber.aka Glycans 1. can be branched or unbranched 3. roots and seeds • glycogen . wood .Polysaccharides . homopolysaccharides vs heteropolysaccharides 2.plants. used by animals and plants as a compact storage form of CHOs 4. common examples • starch .liver of mammals • cellulose .

wheat and barley a linear polysaccharide of glucose units .Starch = amylose + amylopectin found in corn. rice. potato.

Amylopectin .a branched form of amylose .

Structure of starch glycogen (animal starch) is like starch. but more highly branched .

in a fermentation vat — breaks the sugar chains down even further to yield the simple sugar glucose. which is almost entirely glucose.which is produced by Aspergillus. 2.High-fructose corn syrup High-fructose corn syrup is produced by milling corn to produce corn starch. 1.wikipedia.Glucoamylase . http://en.The enzyme xylose isomerase (aka glucose isomerase) then converts some of the glucose to a mixture of about 42% fructose and 50–52% glucose with some other sugars mixed in. and then adding enzymes that change most of the glucose into fructose. a fungus.org/wiki/High-fructose_corn_syrup . 3.Corn starch is treated with alpha-amylase to produce shorter chains of sugars called oligosaccharides. then processing that starch to yield corn syrup.

Protein glycosylation: A post-translational modification • Sugars covalently attached to the polypeptide as oligosaccharide chains containing 4 to 15 sugars • Sugars frequently comprise 50% or more of the total molecular weight of a glycoprotein • Most glycosylated proteins are either secreted or remain membranebound • Glycosylation is the most abundant form of post-translational modification • Glycosylation confers resistance to protease digestion by steric protection • Important in cell-cell recognition .

Blood group antigens on erythrocyte surface • The O substance is a tetrasaccharide which is missing the 5th residue and does not elicit an antibody response (non-antigenic). • The A antigen and B antigen are pentasaccharides which differ in composition of the 5th sugar residue .

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