Transcript CE Chapter 17 and 18

CHAPTER 17 AND 18
CONCURRENT ENROLLMENT
CARBOHYDRATES
• BIOMOLECULE
– Organic compounds essential for life
• BIOCHEMISTRY
– Study of compounds and processes associated with living organisms
• CARBOHYDRATES
– A polyhydroxyl aldehyde or ketone, or substance that yields such
compounds upon hydrolysis
• Monosaccharide
– A simple carbohydrate most commonly consisting of 3 to 6 carbon
atoms
• Disaccharide
– A carbohydrate formed by the combination of two monosaccharides
• Polysaccharide
– A carbohydrate formed by the combination of many monosaccharide
units
STEREOCHEMISTRY
• Enantiomers
– Mirror images like a hand or 1 and d
glyceraldehyde
• Chiral
– A term for compounds or objects that cannot be
superimposed on their mirror image
• Chiral carbon
– Carbon atom with four different groups attached
• Learning checks on pages 535 and 537
FISHER PROJECTIONS
• Method to look at chiral molecules three-dimensional
• With the acid group or the ketone group or the
aldehyde group facing up
• The farthest away chiral carbon look at the hydroxyl
or amino group this tells you if it is a D or L family
• If the last group is on the right side it is in the D
family
• If the last group is on the left side it is in the L family
• Learning check page 539 and 540
Continue
• Levorotatory
– Rotates plane-polarized light to the left
• Dextrorotatory
– Rotates plane-polarized light to the right
• Optically active molecule
– A molecule that rotates the plane of polarized light
• Living organisms are made up largely of chiral
substances
• Both enantiomers will not be found together in the
same biological system
• L-lactic acid is found in muscles, while D-lactic acid
is found in sour milk
MONOSACCHARIDES
• Table 17.1 page 541
• With an aldeyde group in a monosaccharide
you have a prefix aldo• With a ketone group you will have a prefix
keto• Learning check page 541
• Figure 17.8 gives you the family of D aldoses.
MEMORIZE THESE
PROPERTIES
• Most monosaccharides are sugars, because they taste
sweet
• Table 17.2 page 543
• Monosaccharides with at least five carbons exist
predominantly as CYCLIC HEMIACETALS AND
HEMIKETALS
• Overhead
• Pyranose ring
– A six-membered sugar ring system containing an oxygen
atom
Continue
• Haworth structure
– Three-dimensional carbohydrate structures
• Anomeric carbon
– An acetal, ketal, hemiacetal, or hemiketal carbon atom giving rise to
two stereoisomers
• Anomers
– Stereoisomers that differ in the three-dimensional arrangement of
groups at the carbon of an acetal, ketal, hemiacetal or hemiketal
• Furanose ring
–
–
–
–
–
A five-membered sugar ring system containing an oxygen atom
Page 544 look at drawings
Anomeric carbon is to the right of the oxygen
Hydroxyl group down is α and up is β
Learning check page 546
REACTIONS
• Oxidation
– Aldehydes and ketones that have adjacent -OH groups are oxidized by
alkaline solutions containing Cu2+
– A sugar that can be reduced by Cu2+ is called a REDUCING SUGAR
– Page 547 look at general reaction
• Phosphate ester
– Monosaccharides behave as an alcohol and reacts with an acid to form
and ester
– Important Intermediates in the carbohydrate metabolism
• Glycoside
– Another name for a carbohydrate containing an acetal or ketal group
– Page 548 glycosidic linkage and learning check
Important monosaccharides and
disaccharides
• Read pages 548-558
• Know (draw) ribose, glucose, galactose and maltose
• DNA AND RNA are pentoses and are essential in
protein synthesis and the transfer of genetic material
• Glucose is a hexose and is found in honey and also
known as blood sugar
• Galactose is a hexose and similar to glucose. This is
found in mammal milk
Continue
• Maltose is formed from two α-D-glucose linking this
is malt sugar
• Lactose is formed from a β-D-Galactose and α-Dglucose, this makes up 5% of cow’s milk and 7% of
human milk
• Surcose is formed from a α-D-glucose and β-Dfructose, found in fruits and sugar cane
• Polysaccharides
– Not water soluble
– Table 17.4 and overhead
– Starch, glycogen, cellulose
CHAPTER 18
• Lipid
– A biological compound that is soluble only in NONPOLAR
SOLVENTS
• Simple lipid
– A ester-containing lipid with just two types of components: an alcohol
and one or more fatty acids
• Complex lipid
– An ester-containing lipid with more than two types of components: an
alcohol, fatty acids – plus others
• Fatty acids are the fundamental building block for many lipids
– They are long-chain carboxylic acids
– It is the long nonpolar chain on the fatty acid that gives the oily
characteristics of fats
– In the physiological pH the polar head exists as the carboxylate anion –
COO-
FATTY ACIDS
• Micelle
– A spherical cluster of molecules in which the polar portions of the
molecules are on the surface and the nonpolar portions are located in
the interior.
• Figure 18.3 page 567
• Fatty acids found in natural lipids have the following
characteristics
– They are usually straight-chain carboxylic acids (no branching)
– The sizes of most common fatty acids range from 10 to 20 carbons
– Fatty acids usually have an even number of carbon atoms (including the
carboxyl group carbon)
– Fatty acids can be saturated (containing no double bonds between
carbons). Apart from the carboxyl group and double bonds, there are
usually no other functional groups
Continue
• Unsaturated fatty acids usually contain double bonds
in the cis- configuration
– This forms kinks that result in weaker intermolecular
forces, low melting points and are usually liquid at room
temperature
– Overheads
• Essential fatty acids
– Fatty acids needed for reactions in the body, but not made
in the body
– Linoleic acid and linolenic acid, these are found in fish and
plant oils
– They regulate blood pressure, blood clotting, blood lipid
levels etc.
STRUCTURE OF FATS AND OILS
• In fats and oils, the alcohol portion is always derived
from glycerol, and the acid portion comes from the
fatty acids
• Overhead
• Learning check 18.1 570
• Fat
– A triglyceride that is a solid at room temperature
• Oil
– A triglyceride that is a liquid at room temperature
• They differ in the degree of unsaturation
• Saturated fats influence blood cholesterol
CHEMICAL PROPERTIES
• Hydrolysis
– Fats and oils can react with water (only when in the presence of acid or
lipase, enzyme) it will reverse the ester formation
– Glycerol and fatty acids are reformed
– Learning check 18.2 page 572
• Saponification
– Overhead
– When triglycerides react with a strong base it will form soap (glycerol
with a salt)
– Sodium salts are found in the cake soaps
– Potassium salts are found in shaving creams and liquid soaps
– Overhead
– Learning check 18.3 page 573
Continue
• Hydrogenation
– Double bonds of unsaturated fats can be broken when reacting with
hydrogen in the presence of a catalyst
– This will decrease the degree of unsaturation and increase the melting
point
– This is how margarine and peanut butter are made
– During hydrogenation some fatty acids with the common cisconfiguration are isomerized into trans-form. Like margarine
• Study skills page 575
• Wax
– An ester of a long-chain fatty acid and a long-chain alcohol
– Are water-insoluble
– In nature are found on feathers, leaves or fruits
• Phosphoglycrides
– A complex lipid containing glycerol, fatty acids, phosphoric acid, and
an alcohol component
Continue
• Phospholipid
– A phosphorus-containing lipid
– Overhead
• Lecithin
• A phosphoglyceride containing choline
–
+
– HO-CH2CH2-N(CH3)3
– This makes one end hydrophilic and the rest of the molecule
hydrophobic
– This is very important in forming cell membranes
• Cephalin
– A phospholyceride containing ethanolamine or serine
–
+
+
HO-CH2CH2-NH3 and HO-CH2CH-NH3
COO-
Continue
• Sphingolipids
– A complex lipid containing sphingosine (page 578), a fatty
acid, phosphoric acid, and choline
– Large amounts of sphingomyelin are found in the brain and
nerve tissue
• Glycolipid
– A complex lipid containing a sphingosine, a fatty acid, and
a carbohydrate
– Page 578
– When a body cannot break down these complex lipids, due
to a genetic inability to form an enzyme. This causes
several human diseases like Tay-Sachs
BIOLOGICAL MEMBRANES
• Prokaryotic cell
– A simple unicellular organism that contains no
nucleus and no membrane-enclose organelles
• Eukaryotic cell
– A cell containing membrane-enclosed organelles,
particularly a nucleus
• Organelle
– A membrane-encased body in the interior of a cell
Continue
• Most cells are made up of 40% protein and 60%
lipids
– Phosphoglycerides (lecithin and cephlin), sphingomyelin,
and cholesterol
• Fluid-mosaic model
– A model of membrane structure in which proteins are
embedded in a flexible lipid bilayer
• Lipid bilayer
– A structure found in membranes, consisting of two sheets
of lipid molecules arranged so that the hydrophobic
portions are facing each other
• Overhead
STEROIDS
• A compound containing four rings fused in a particular
pattern
• The most abundant steroid in the human body is
cholesterol (very important)
• Overhead
• Found in cell membranes and is the building blocks for
sex hormones, vitamin D, bile salts, etc.
• Synthesized in the liver
• Bile salts
– Yellowish brown or green liver secretion that is stored in the
gallbladder
HORMONES
• Chemical messenger secreted by specific glands and
carried by the blood to a target tissue, where it triggers a
particular response
• Adrenocorticoids
– Produced in the adrenal glands by the kidney
– Regulates the ion concentration (mainly sodium ions) in body
fluids
– Enhances carbohydrate metabolism
•
•
Sex hormones
Testosterone
– Male hormone for development
– When these steroids are given to the body it can increase
muscular development but can cause testicular atrophy or a
decrease in sperm count
Continue
• Female hormones used in the reproductive
process
• Estrogens
– Estradiol and estrone
• Progesterone
• Prostaglandins
– A substance derived from unsaturated fatty acids,
with hormone-like effects on a number of body tissues
– These can regulate menstruations, prevent
conception, stimulate blood clotting, it can even be
used as an aerosol for asthma
– Overheads