1. Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@latech.edu Office: 311 Carson Taylor Hall ; Phone: 318-257-4941; Office Hours: MTW 9:00 am - 11:00 am; TR 9:00 - 10:00 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

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

3. Chapter 18: Carbohydrates 18.1 Biochemistry-An Overview, 593 18.2 Occurrence and Functions of Carbohydrates, 593 18.3 Classification of Carbohydrates, 594 18.4 Chirality: Handedness in Molecules, 595 18.5 Stereoisomerism: Enantiomers and Diastereomers, 599 18.6 Designating Handedness Using Fischer Projection Formulas, 600 18.7 Properties of Enantiomers, 604 18.8 Classification of Monosaccharides, 607 18.9 Biochemically Important Monosaccharides, 609 18.10 Cyclic Forms of Monosaccharides, 612 18.11 Haworth Projection Formulas, 615 18.12 Reactions of Monosaccharides, 618 18.13 Disaccharides, 621 18.14 Oligosaccharides, 631 18.15 General Characteristics of Polysaccharides, 634 18.16 Storage Polysaccharides, 635 18.17 Structural Polysaccharides, 637 18.18 Acidic Polysaccharides, 640 18.19 Dietary Considerations and Carbohydrates, 641 33 CHEM 121 Winter 20133

4. 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

5. Drawing Sugar Molecules Aldehyde Polyhydroxy aldehyde Ketone Polyhydroxy ketone Linear structure-Fischer projection CHEM 121 Winter 20135 hydroxy

6. 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

7. 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

8. 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

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

10. 1) Give names of the following carbohydrates. Identify the chiral carbon atoms with * CHEM 121 Winter 201310

11. 2) Circle the correct classifications that apply to the following carbohydrates. CHEM 121 Winter 201311

12. 2) Circle the correct classifications that apply to the following carbohydrates. CHEM 121 Winter 201312

13. 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 201313

14. 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 201314

15. 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 201315

16. 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 201316

17. How you get cyclic hemiacetal form of the ketohexose sugar D- fructofuranose with  -anomeric. CHEM 121 Winter 201317

18. How you get cyclic hemiacetal form of the ketohexose sugar D-glucopyranose with  - anomeric. CHEM 121 Winter 201318

19. 4) a) Complete the following diagram to get the cyclic hemiacetal form of the aldohexose sugar D- glucopyranose with  -anomeric configuration. CHEM 121 Winter 201319

20. 4) b) Draw the structure of  -D-mannopyranose CHEM 121 Winter 201320

21. 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 201321

22. 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 201322

23. 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 201323

24. Glycosidic bonds Glycosidic bond- covalent bond between a hemiacetal or hemiketal and an alcohol. CHEM 121 Winter 201324

25. 6) What are the following? What is/are glucosidic linkage found in them? a) Starch: b) Amylopectin: c) Glycogen: d) Cellulose CHEM 121 Winter 201325

26. 7) Answer following question about glycosidic bond of the di-, oligo- and poly- saccharides. a) Name of the following glucoside CHEM 121 Winter 201326

27. 8) b) Name of the following N-Glycoside c) Name of the following glucoside. CHEM 121 Winter 201327

28. 8) d) The following is a part of a cellulose polymeric chain. What is the type of glucosidic linkage? CHEM 121 Winter 201328

29. 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 201329

30. Nucleic Acids Bases Purines pyrimidines CHEM 121 Winter 201330

31. 8) e) What is DNA? Describe the components. CHEM 121 Winter 201331

32. 8) f) What is RNA? Describe the components. CHEM 121 Winter 201332