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Chemistry 121 Winter 17 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@latech.edu.

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Presentation on theme: "Chemistry 121 Winter 17 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) E-mail: upali@latech.edu."— Presentation transcript:

1 Chemistry 121 Winter 17 Introduction to Organic Chemistry and Biochemistry Instructor Dr. Upali Siriwardane (Ph.D. Ohio State) Office: 311 Carson Taylor Hall ; Phone: ; Contact me trough if you have questions Online Tests on Following days December 16, 2016: Test 1 (Chapters 12-13) January 23, 2017 : Test 2 (Chapters 14-16) February 10, 2017 : Test 3 (Chapters 17-19) February 22, 2017 : Test 4 (Chapters 20-22) February 23, 2017: Make Up Exam: Chapters 12-22)

2 Chapter 18 and GHW#8 Questions & Slides
Carbohydrates CHEM 121 Winter 2016

3 Chapter 18: Carbohydrates
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 • 18-8Classification of Monosaccharides Biochemically Important Monosaccharides 18-10 Cyclic Forms of Monosaccharides 18-11 Haworth Projection Formulas 18-12 Reactions of Monosaccharides 18-13 Disaccharides 18-14 Oligosaccharides 18-15 General Characteristics of Polysaccharides 18-16 Storage Polysaccharides 18-17 Structural Polysaccharides 18-18 Acidic Polysaccharides 18-19 Dietary Considerations and Carbohydrates 18-20 Glycolipids and Glycoproteins: Cell Recognition CHEM 121 Winter 2016

4 What is Biochemistry Biochemistry is the study of the chemical processes occurring in living matter. Chemical Processes Involving carbohydrates (chapter 18) Involving Lipid (chapter 19) Involving Proteins (chapter 20) Involving Genetics (RNA &DNA) (chapter 22) Involving Vitamins & Minerals (chapter 21) CHEM 121 Winter 2016

5 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: CnH2nOn or Cn(H2O)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 2017

6 Drawing Sugar Molecules
Linear structure-Fischer projection Aldehyde Ketone hydroxy Polyhydroxy aldehyde Polyhydroxy ketone CHEM 121 Winter 2016

7 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 2017

8 CHEM 121 Winter 2017

9 Constitutional Isomers
Skeletal (Chp. 12) Functional (Chp. 14) Positional (Chp. 12) Stereoisomers Conformational (Chp.12) Geometric (Chp. 13) Enantiomers (Optical) (Chp. 16) CHEM 121 Winter 17

10 Chirality: Handedness in Molecules
Most monosaccharaides exist in two forms: a “left handed” and “right handed” form due to chiral carbon atoms L isomers D isomers CHEM 121 Winter 2017

11 Chirality and Optical Activity
L isomers D isomers Polarimeter assigns D and L isomers D-rotated to right L-rotates to left CHEM 121 Winter 2016

12 Cyclic anomeric forms: a- and b- forms
Fischer structure Haworth structures ALDEHYDE sugar or aldoses  + alcohol  --- hemiacetal (cyclic ring) CHEM 121 Winter 2017

13 1) Give names of the following carbohydrates
1) Give names of the following carbohydrates. Identify the chiral carbon atoms with * CHEM 121 Winter 2017

14 2) Circle the correct classifications that apply to the following carbohydrates.
CHEM 121 Winter 2017

15 2) Circle the correct classifications that apply to the following carbohydrates.
CHEM 121 Winter 2017

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 2017

17 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 2017

18 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 2017

19 2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the Fisher Projection structure for following aldohexoses. CHEM 121 Winter 2017

20 How you get cyclic hemiacetal form of the hexose sugars pyran with b- and a anomeric forms.
a-D-glucopyranose b-D-fructofuranose Haworth Projection Formula-cyclic CHEM 121 Winter 2017

21 How you get cyclic hemiacetal form of the ketohexose sugar D-fructofuranose with b-anomeric.
b-D-fructofuranose D-fructose Fisher Projection Formula-Linear Haworth Projection Formula-cyclic CHEM 121 Winter 2017

22 How you get cyclic hemiacetal form of the ketohexose sugar D-glucopyranose with b-anomeric.
b-D-glucopyranose D-glucose Haworth Projection Formula- cyclic Fisher Projection Formula- Linear CHEM 121 Winter 2017

23 4) a) Complete the following diagram to get the cyclic hemiacetal form of the aldohexose sugar D-glucopyranose with b-anomeric configuration. CHEM 121 Winter 2017

24 b) Draw the structure of b-D-mannopyranose
4) b) Draw the structure of b-D-mannopyranose CHEM 121 Winter 2017

25 4) c) What is the difference between
pynanose and furanose types of sugars? d) What is the difference between a and b forms of cyclic hemiacetal forms of sugars? CHEM 121 Winter 2016

26 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 a-anomeric CHEM 121 Winter 2017

27 5) b) Use the procedure we used in problem 4 to get linear form of the hexoaldose sugar from cyclic D-sugarpyranose with b-anomeric CHEM 121 Winter 2017

28 Glycosidic bonds Glycosidic bond- covalent bond between a hemiacetal or hemiketal and an alcohol. CHEM 121 Winter 2017

29 Disaccharides Linked by glycosidic bond. (Maltose)
Glucose +Glucose -> (a-1-4) Glucose +Glucose -> (a-1-4) maltose Galactose+Glucose -> (b-1-4) lactose CHEM 121 Winter 2016

30 Starch and Amylopectin (Glycogen)
a) Starch: b) Amylopectin: c) Glycogen: CHEM 121 Winter 2016

31 Cellulose CHEM 121 Winter 2016

32 6) What are the following? What is/are glucosidic linkage found in them?
d) Cellulose CHEM 121 Winter 2017

33 What carbohydrates are found in them?
The glycemic index is a system that measures how quickly a specific food can raise your blood sugar levels Fiber-rich foods CHEM 121 Winter 2017

34 a) Name of the following o-glucoside
7) Answer following question about glycosidic bond of the di-, oligo- and poly- saccharides. a) Name of the following o-glucoside CHEM 121 Winter 2017

35 b) Name of the following N-Glycoside
8) b) Name of the following N-Glycoside c) Name of the following O-glucoside. CHEM 121 Winter 2017

36 8) d) The following is a part of a cellulose polymeric chain. What is the type of glucosidic linkage? CHEM 121 Winter 2016

37 Purines and Pyrimidines: DNA Bases
RNA CHEM 121 Winter 2017

38 e) What is DNA? Describe the components.
8) e) What is DNA? Describe the components. CHEM 121 Winter 2016

39 Nucleic Acids phosphate-group+pentose-sugar+Base
D-Ribose D-deoxyribose Deoxypentose sugar or D-deoxyribose: ribose-derivative with an oxygen missing on C-2. CHEM 121 Winter 2016

40 Nucleic Acids Bases Purines pyrimidines CHEM 121 Winter 2016

41 DNA-Deoxyribo-Nucleic Acid
CHEM 121 Winter 2016

42 CHEM 121 Winter 2016

43 8) f) What is RNA? Describe the components. CHEM 121 Winter 2016

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