Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Office Hours: MTW 9:00 am - 11:00 am; TR 9: :00 am & 1:00-2:00 pm. December 20, Test 1 (Chapters 12-13) January 27 Test 2 (Chapters 14-16) February 14 Test 3 (Chapters 17-19) February 26, Test 4 (Chapters 20-22) February 27, 2014, Make Up Exam: Bring Scantron Sheet 882-E Chemistry 121(01) Winter 2014

Chapter 18 and GHW#8 Questions & Slides Carbohydrates CHEM 121 Winter 20132

Chapter 18: Carbohydrates 18.1 Biochemistry-An Overview, Occurrence and Functions of Carbohydrates, Classification of Carbohydrates, Chirality: Handedness in Molecules, Stereoisomerism: Enantiomers and Diastereomers, Designating Handedness Using Fischer Projection Formulas, Properties of Enantiomers, Classification of Monosaccharides, Biochemically Important Monosaccharides, Cyclic Forms of Monosaccharides, Haworth Projection Formulas, Reactions of Monosaccharides, Disaccharides, Oligosaccharides, General Characteristics of Polysaccharides, Storage Polysaccharides, Structural Polysaccharides, Acidic Polysaccharides, Dietary Considerations and Carbohydrates, CHEM 121 Winter 20133

Carbohydrates Organic compounds containing many -OH groups (polyhydroxy), and aldehydes or ketones functional groups. They are called sugars. Aldoses: Aldehyde sugars are called aldoses. Ketoses: Ketone sugars are called ketoses. Formula for Cabohydrates: C n H 2n O n or C n (H 2 O) n (hydrates of C) n= number of atoms Monosaccharides They consist of one sugar containing 3,4,5,6 and 7 carbon atoms Disaccharides Polysaccharides CHEM 121 Winter 20134

Drawing Sugar Molecules Aldehyde Polyhydroxy aldehyde Ketone Polyhydroxy ketone Linear structure-Fischer projection CHEM 121 Winter hydroxy

Types of sugars Number fo carbon atoms Triose sugar units containing three carbon atoms Tetroses sugar units containing four carbon tomsa Pentoses sugar units containing five carbon atoms Hexoses sugar units containing six carbon atoms CHEM 121 Winter 20136

Chirality: Handedness in Molecules left handed right handed Most monosaccharaides exist in two forms: a “left handed” and “right handed” form due to chiral carbon atoms CHEM 121 Winter 20137

Chirality and Optical Activity Polarimeter assigns D and L isomers D-rotated to right L-rotates to left L D L isomers D isomers CHEM 121 Winter 20138

Cyclic anomeric forms:  - and  - forms Fischer structure Haworth structures ALDEHYDE sugar or aldoses + alcohol --- hemiacetal (cyclic ring) CHEM 121 Winter 20139

1) Give names of the following carbohydrates. Identify the chiral carbon atoms with * CHEM 121 Winter

2) Circle the correct classifications that apply to the following carbohydrates. CHEM 121 Winter

2) Circle the correct classifications that apply to the following carbohydrates. CHEM 121 Winter

2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses. CHEM 121 Winter

2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses. CHEM 121 Winter

2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses. CHEM 121 Winter

2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for following aldohexoses. CHEM 121 Winter

How you get cyclic hemiacetal form of the ketohexose sugar D- fructofuranose with  -anomeric. CHEM 121 Winter

How you get cyclic hemiacetal form of the ketohexose sugar D-glucopyranose with  - anomeric. CHEM 121 Winter

4) a) Complete the following diagram to get the cyclic hemiacetal form of the aldohexose sugar D- glucopyranose with  -anomeric configuration. CHEM 121 Winter

4) b) Draw the structure of  -D-mannopyranose CHEM 121 Winter

4) c) What is the difference between pynanose and furanose types of sugars? d) What is the difference between  and  forms of cyclic hemiacetal forms of sugars? CHEM 121 Winter

5) Convert the hemiacetal cyclic structures (Haworth Projections) for following carbohydrates to Fischer Projections. a) Use the procedure we used in problem 4 to get linear form of the hexoketose sugar from cyclic D-fructofuranose with  -anomeric CHEM 121 Winter

5) b) Use the procedure we used in problem 4 to get linear form of the hexoaldose sugar from cyclic D-sugarpyranose with  -anomeric CHEM 121 Winter

Glycosidic bonds Glycosidic bond- covalent bond between a hemiacetal or hemiketal and an alcohol. CHEM 121 Winter

6) What are the following? What is/are glucosidic linkage found in them? a) Starch: b) Amylopectin: c) Glycogen: d) Cellulose CHEM 121 Winter

7) Answer following question about glycosidic bond of the di-, oligo- and poly- saccharides. a) Name of the following glucoside CHEM 121 Winter

8) b) Name of the following N-Glycoside c) Name of the following glucoside. CHEM 121 Winter

8) d) The following is a part of a cellulose polymeric chain. What is the type of glucosidic linkage? CHEM 121 Winter

Nucleic Acids phosphate-group+pentose-sugar+Base D-Ribos D-deoxyribose Deoxysugar or D-deoxyribose: ribose-derivative with an oxygen missing on C-2. CHEM 121 Winter

Nucleic Acids Bases Purines pyrimidines CHEM 121 Winter

8) e) What is DNA? Describe the components. CHEM 121 Winter

8) f) What is RNA? Describe the components. CHEM 121 Winter