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Introduction to Organic Chemistry and Biochemistry
Instructor Dr. Upali Siriwardane (Ph.D. Ohio State)
E-mail: [email protected]
Office: 311 Carson Taylor Hall ; Phone: 318-257-4941;
Contact me trough e-mail 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)
Chemistry 121 Winter 17
1
Chapter 18 and GHW#8 Questions & Slides
Carbohydrates
CHEM 121 Winter 2016 2
Chapter 18: Carbohydrates
CHEM 121 Winter 20163
18-1 Biochemistry—An Overview
18-2 Occurrence and Functions of Carbohydrates
18-3 Classification of Carbohydrates
18-4 Chirality: Handedness in Molecules
18-5 Stereoisomerism: Enantiomers and Diastereomers
18-6 Designating Handedness Using Fischer Projection Formulas
18-7 Properties of Enantiomers • 18-8Classification of Monosaccharides
18-9 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
What is BiochemistryBiochemistry 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)
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CarbohydratesOrganic 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 atomsMonosaccharides
They consist of one sugar containing 3,4,5,6 and 7 carbon atoms
Disaccharides Polysaccharides
CHEM 121 Winter 2017 5
Drawing Sugar Molecules
CHO
OHH
HHO
OHH
OHH
CH2OH
Glucose
CH2OH
O
HHO
OHH
OHH
CH2OH
Fructose
Aldehyde
Polyhydroxyaldehyde
Ketone
Polyhydroxyketone
Linear structure-Fischer projection
CHEM 121 Winter 2016 6
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
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CHEM 121 Winter 2017 8
CH 3CH 2CH 2CH 3 CH 3CHCH 3
CH3
CH 3CH 2CH 2 CH 3CH CH 3
Br Br
CH 3CH 2OH CH 3OCH 3
CH3
HHH
CH3H
C CH
Br
H
BrC C
H
Br
Br
H
CH3
H H
CH3
H H
CO2H
CH3
H OHC
CO2H
CH3
H O HC
Constitutional Isomers
Positional (Chp. 12)
Skeletal (Chp. 12)
Enantiomers (Optical) (Chp. 16)
Functional (Chp. 14)
StereoisomersConformational (Chp.12)Geometric (Chp. 13)
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Chirality: Handedness in Molecules
Most monosaccharaides exist in two forms: a “left handed” and “right handed” form due to chiral carbon atoms
CHO
HO H
C
CH OH2
CH OH2
H
CHO
HO
CHO
H
C
CH OH2
OH
CH OH2
H
CHO
OH
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D isomers L isomers
Chirality and Optical Activity
Polarimeter assigns D and L isomers
D-rotated to rightL-rotates to left
L D
L isomers D isomers
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Cyclic anomeric forms: a- and b- forms
Fischer structure Haworth structures
ALDEHYDE sugar or aldoses + alcohol --- hemiacetal (cyclic ring)
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1) Give names of the following carbohydrates. Identify the chiral carbon atoms with *
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2) Circle the correct classifications that apply to the following carbohydrates.
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2) Circle the correct classifications that apply to the following carbohydrates.
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2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for
following aldohexoses.
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2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for
following aldohexoses.
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2) Complete the names, circle carbon atom numbers of the OH group which is on the left and the structure for
following aldohexoses.
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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.
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How you get cyclic hemiacetal form of the hexose sugars pyran with b- and a
anomeric forms.
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b-D-fructofuranosea-D-glucopyranose
Haworth Projection Formula-cyclic
How you get cyclic hemiacetal form of the ketohexose sugar D-fructofuranose with b-anomeric.
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b-D-fructofuranose
D-fructose
Fisher Projection Formula-Linear Haworth Projection Formula-cyclic
How you get cyclic hemiacetal form of the ketohexose sugar D-glucopyranose with b-anomeric.
CHEM 121 Winter 2017 22
Fisher Projection Formula-Linear
Haworth Projection Formula-cyclic
D-glucose
b-D-glucopyranose
4) a) Complete the following diagram to get the cyclic hemiacetal form of the aldohexose sugar D-glucopyranose with b-anomeric configuration.
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4)
b) Draw the structure of b-D-mannopyranose
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4) c) What is the difference between pynanose and furanose types of sugars?
d) What is the difference between a and bforms of cyclic hemiacetal forms of sugars?
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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
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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
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Glycosidic bonds
Glycosidic bond- covalent bond between a hemiacetal or hemiketal and an alcohol.
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DisaccharidesLinked by glycosidic bond.
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Glucose +Glucose -> (a-1-4) maltoseGlucose +Glucose -> (a-1-4)
(Maltose)
Galactose+Glucose -> (b-1-4) lactose
a) Starch:
b) Amylopectin:
c) Glycogen:
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Starch and Amylopectin (Glycogen)
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Cellulose
6) What are the following? What is/are glucosidic linkage found in them?
d) Cellulose
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What carbohydrates are found in them?
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The glycemic index is a system that measures how quickly a specific food can raise your blood sugar levels
Fiber-rich foods
7) Answer following question about glycosidic bond of the di-, oligo- and poly-saccharides.a) Name of the following o-glucoside
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8)b) Name of the following N-Glycoside
c) Name of the following O-glucoside.
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8)d) The following is a part of a cellulose polymeric chain. What is the type of glucosidiclinkage?
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Purines and Pyrimidines: DNA Bases
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DNA
RNA
DNA
8)e) What is DNA? Describe the components.
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Nucleic Acidsphosphate-group+pentose-sugar+Base
D-Ribose D-deoxyribose
• Deoxypentose sugar or D-deoxyribose: ribose-derivative with an oxygen missing on C-2.
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Nucleic Acids
Bases
Purines pyrimidinesCHEM 121 Winter 2016 40
DNA-Deoxyribo-Nucleic Acid
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8)f) What is RNA? Describe the components.
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