ib dp2 chemistry option b: human biochemistry
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IB DP2 Chemistry Option B: Human Biochemistry. What compounds are living organisms built from?. Option B: Human Biochemistry. B1 Energy (0.5 hour) B.1.1 Calculate the energy value of a food from enthalpy of combustion data. B2 Proteins (3 hours) - PowerPoint PPT PresentationTRANSCRIPT
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IB DP2 ChemistryOption B:
Human BiochemistryWhat compounds are living organisms built from?
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Option B: Human Biochemistry
B1 Energy (0.5 hour)B.1.1 Calculate the energy value of a food from enthalpy of combustion data.
B2 Proteins (3 hours)B.2.1 Draw the general formula of 2-aminoacids.B.2.2 Describe the characteristic propertiesof 2-amino acidsB.2.3 Describe the condensation reaction of2-amino acids to form polypeptides.B.2.4 Describe and explain the primary,secondary (α-helix and β-pleated sheets), tertiary and quaternary structure of proteins.B.2.5 Explain how proteins can be analysed by chromatography and electrophoresis.B.2.6 List the major functions of proteins in the body.
B3 Carbohydrates (3 hours)B.3.1 Describe the structural features of monosaccharides.B.3.2 Draw the straight-chain and ring structural formulas of glucose and fructose.B.3.3 Describe the condensation of monosaccharides to form disaccharides and polysaccharides.B.3.4 List the major functions of carbohydrates in the human body.B.3.5 Compare the structural properties of starch and cellulose, and explain why humans can digest starch but not cellulose.B.3.6 State what is meant by the term dietary fibre.B.3.7 Describe the importance of a diet high in dietary fibre.
B4 Lipids (3.5 hours)B.4.1 Compare the composition of the three types of lipids found in the human body.B.4.2 Outline the difference between HDL and LDL cholesterol and outline its importance.
B.4.3 Describe the difference in structure between saturated and unsaturated fatty acids.B.4.4 Compare the structures of the two essential fatty acids linoleic (omega–6 fatty acid) and linolenic (omega–3 fatty acid) and state their importance.B.4.5 Define the term iodine number and calculate the number of C=C double bonds in an unsaturated fat/oil using addition reactions.B.4.6 Describe the condensation of glycerol and three fatty acid molecules to make a triglyceride.B.4.7 Describe the enzyme-catalysed hydrolysis of triglycerides during digestion.B.4.8 Explain the higher energy value of fats as compared to carbohydrates.B.4.9 Describe the important roles of lipids in the body and the negative effects that they can have on health.
B5 Micronutrients and macronutrients (2 hours)B.5.1 Outline the difference between micronutrients and macronutrients.2 Micronutrients are substances required in very small amounts (mg or μg) and that mainly function as a co-factor of enzymes (<0.005% body weight).B.5.2 Compare the structures of retinol (vitamin A), calciferol (vitamin D) and ascorbic acid (vitamin C).B.5.3 Deduce whether a vitamin is water- or fat-soluble from its structure.B.5.4 Discuss the causes and effects of nutrient deficiencies in different countries and suggest solutions.
B6 Hormones (3 hours)B.6.1 Outline the production and function of hormones in the body.B.6.2 Compare the structures of cholesterol and the sex hormones.B.6.3 Describe the mode of action of oral contraceptives.
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Image: http://en.wikipedia.org/wiki/Human_body
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What are the chemical constituents of food?
Image: http://en.wikipedia.org/wiki/File:Salami_sandwich.jpg
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Food builds the bodies of living organisms
Nutrients: food components for growth, energy and replacement.
WaterMacronutrients Proteins built from amino acids Carbohydrates LipidsMicronutrients Vitamins Minerals
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Energy in food
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Energy density of foods
Food componentEnergy density
kJ/g kcal/gFat 37 9Proteins 17 4Carbohydrates 17 4Organic acids 13 3Fiber 8 2Ethanol 29 7
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Too much or too little?Caloric starvation: Weakness, anaemia, muscle wasting.....Excessive foood: Fat storage, diabetes, cardiovascular diseases.
Energy: Young active male: 14700kJ (~3500 Cal) Young active female: 8400 kJ (~2000 Cal) At rest: ~60%
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MetabolismCatabolism: breaks down organic matter and harvests energy by way of cellular respirationAnabolism: uses energy to construct components of cells such as proteins and nucleic acids
Image: http://en.wikipedia.org/wiki/File:ATP-3D-vdW.png
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Energy units (Joules, but…) 1 Calorie = 1000 calories = 1 kcal 1 Cal: increases 1kg H2O by 1oC
1 cal: increases 1g H2O by 1oC
1 Cal = 4.18 kJ 1 cal = 4.18 J
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Calorimeter- burns food to heat water
Images: http://www.chem.ufl.edu/~itl/2045/lectures/lec_9.html, http://www.azosensors.com/equipment-details.aspx?EquipID=285
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Example:15.0 g of apple raises the temperature of 200g water by 45.3oC.Heat capacity of the container: = 85JoC-1
Calculate the energy released by the apple and the energy density of the apple.
Heat produced = heat absorbed by water + heat absorbed by calorimeter
Image: http://en.wikipedia.org/wiki/Apple
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Micronutrients
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Macronutrients and micronutrients Macronutrients- need in relatively large
amounts >0.0005% of body weight protein, fat, carbohydrates, minerals (na, Mg, K, Ca,
P, S, Cl)
Micronutrients vitamins and trace minerals
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Vitamins- water or fat soluble Vitamin A (retinol) Vitamin C (ascorbic acid) Vitamin D (calciferol)
Malnutrition and deficiency diseases
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Proteins
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Proteins built from 2-amino acids
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Zwitterion
Image: http://en.wikipedia.org/wiki/Zwitterion
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Image: http://en.wikipedia.org/wiki/File:Amino_Acids.svg
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…joined by peptide bonds in a primary structure
Image: http://en.wikipedia.org/wiki/Peptide_bond
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Secondary and tertiary structures
Image: http://en.wikipedia.org/wiki/Secondary_structure#Secondary_structure
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Chromatography
Image: http://glossary.periodni.com/glossary.php?en=paper+chromatography
Image: http://en.wikipedia.org/wiki/Planar_chromatography
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PAGE Polyacrimide Gel Electrophoresis
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Electrophoresis
Amino acid
pH of isoelectric point
Glutamic acid
3.2
Serine 5.7Histidine 7.6
Move faster to anode
Move faster to cathode
+
-
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Carbohydrates
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Functions in the human body provide energy store energy (as glycogen) precursors dietary fibre
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Calculating empirical and molecular formulae
A substance has the composition by mass 40% carbon, 7% hydrogen and 53% oxygen.Calculate the empirical formula.Calculate the molecular formula of the molecule with a molecular mass of 180g/mol.
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Saccharides- empirical formula CH2O
PentosesHexoses
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Chiral molecule: alpha-D glucose or beta-D-glucose
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Disaccharides
Glycosidic link forms by condensation reaction between monosaccharides
Image: http://en.wikipedia.org/wiki/Disaccharide
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Polysaccharides- amylose and amylopectin
Image: http://en.wikipedia.org/wiki/Polysaccharide
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Cellulose
hydrogen bond between layers
glycosidic bond
Image: http://en.wikipedia.org/wiki/Cellulose
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Lipids
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Lipids
large and diverse group
naturally occurring organic compounds
soluble in nonpolar organic solvents (e.g. ether, chloroform, acetone & benzene)
generally insoluble in water
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Triglycerides Ester of three fatty acid
molecules and a glycerol molecule
Ester-group slightly polar but R-groups large and non-polar insoluble in water.
R normally even number of C, 16-20.
Examples: Stearic acid C17H35CO(OH),
saturated acid (only single bonds) solid(e.g. butter)
Oleic acid: C17H33CO(OH): unsaturated (some double bonds) oil
Example of an unsaturated fat triglyceride. Left part:glycerol, right part from top to bottom: palmitic acid, oleic acid,alpha-linolenic acid. C55H98O6 Image: http://en.wikipedia.org/wiki/Triglyceride
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Phospholipids Fatty acid substituted by phosphor-
choline group and gives a lecithin structure.
More polar than triglycerides and build up the bilayer structure in cell membranes.
Also used as a source of choline.
Image:http://en.wikipedia.org/wiki/Phospholipid
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Phospholipids
Image:http://en.wikipedia.org/wiki/Phospholipid
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Steroids three 6-memberd rings + one 5-memberd ring are
steroid skeleton that is found in many different steroids (e.g. sex hormones) and vitamins (e.g. Vit-D)
Image: http://en.wikipedia.org/wiki/Steroid
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Cholesterol produced mainly in the liver, found in the
bloodstream and body cells present in dairy products, meat and eggs. not water soluble so it must have transport help
in the blood from a protein.
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HDL and LDL HDL high density lipoprotein. 40-55% protein LDL low density lipoprotein. 20-25% protein HDL “good cholesterol”: Prevents the build up of
cholesterol in the arteries. HDL can absorb more cholesterol and carry it away from the arteries.
LDL “bad cholesterol”: Higher cholesterol content can give deposition in arteries plaque, a hard thick substance narrowing of arteries cardiovascular diseases.
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Saturated fats: only single bonds between the carbons in the fatty acid.
common in animal (mammalian) fat (except seals and whales), milk and butter
usually solid at room temperature because regular tetrahedral arrangement makes it possible to pack molecules close together so van der Waals forces are large
Image: http://en.wikipedia.org/wiki/Butter
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Unsaturated fats: one or more double bonds
often found in vegetable oils. usually liquid at room temperature C=C makes it hard to pack chains close together
lower Van der Walls forces the greater the number of double bonds, the lower
m.p. Monounsaturated: only one double bond (e.g. olive
oil, rapeseed oil) Polyunsaturated: more than one double bond (e.g
fish oil)
Image:http://en.wikipedia.org/wiki/Oil
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Linoleic and Linolenic acid Essential fatty acid, EFA: a fatty acid that our body cannot make and
therefore must be present in our food in order for a properly body function.
Linoleic acid with 18 carbon atoms. 2 double bonds. Omega-6 fatty acid the last C=C in the chain is 6 atoms away from the end of the chain; the CH3 group (the omega carbon).
Linolenic acid with18 carbon atoms. 3 double bonds. Omega-3 fatty acid the last C=C is three atoms away from the methyl-group.
Linoleic and linolenic are essential fatty acids. Important precursors for hormone like chemicals as prostaglandin and leukotrienes.
Omega-3 is important for brain development during pregnancy. EFA good effect oncholesterol levels, good health, good circulation,
immune system, etc.
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Iodine numberH2C=CH2 + I2 H2IC=CH2I addition Colourless coloured Colourless Titrate fat solution with iodine solution
measurement of the number of double bonds. 1 mol I2 1 mol double bonds Iodine number: number of grams iodine that adds
to 100g of fat. more double bonds greater iodine number.
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Example: Calculate iodine number of linoleic acid.
1 Linoleic acid + 2 I2 tetraiodo-lionoleic acid
m 280 g 506 gM 280 g/mol 253 g/moln 1 mol 1:2 2 mol
Iodine number = mass of iodine × 100 mass of linoleic acid= 506/280×100= 181
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Example: The iodine number of a fatty acid (Mr = 278g/mol) is 274. Calculate the number of C=C double bonds.
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Hydrolysis of a fat: the reverse reaction from an esterification/condensation reaction.
1 Fat 1 glycerol + 3 fatty acids. catalysed be the enzyme Lipase. The reaction
goes step by step: triglyceride diglyceride monoglyceride
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Fats and carbohydrates as energy sources Both fats and carbohydrates are used in nature as
energy source/storage. React with oxygen and release energy (oxidation-
an exothermic reaction). Carbohydrates contains more oxygen than fats
carbohydrates already more oxidised less energy available
Fats very rich in energy: ~double of carbohydrates
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Positive role of lipids in the human body Energy storage Insulation and protection of organs Steroid hormones Structural component of cell membrane Omega-3 polyunsaturated fatty acids reduce the
risk of heart disease. Poly-unsaturated fats may lower levels of LDL
cholesterol
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Negative effects of lipids include Increased risk of heart disease from elevated
levels of LDL cholesterol and trans fatty acids. The major source of LDL cholesterol is saturated fats, in particular lauric (C12), myristic (C14) and palmetic (C16) acids.
Obesity is a disease in which excess body fat has accumulated to such an extent that health may be negatively affected.
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Hormones
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Hormones produced in endocrine glands Adrenaline Thyroxine Sex hormones Insulin
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Teaching notes
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Links Biological molecules https://
www.khanacademy.org/partner-content/crash-course1/crash-course-biology/v/crash-course-biology-103
Zwitterion and gel electrophoresis https://www.khanacademy.org/science/mcat/biomolecules/amino-acids-and-proteins1/v/isoelectric-point-and-zwitterions