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Biochem Midterm Reviewer
Biochem Midterm Reviewer
Introduction to biochemistry
Biomolecules are polymers
• Biochem is the chemistry of living organism. If its
• Biopolymers- macromolecules created by joining
alive, biochemists will study it.
many smaller organic molecule (monomers)
• Biochemistry takes place at the molecular level of
• Condensation reaction- join monomers (water is
organisms.
removed in the process)
• These molecules make up like; bioinorganic molecule
• Residue- each monomer in a chain
(Water 70%, Inorganic salts 5%)[contains elements
other than C, H, O, N, S, & P], bioorganic molecule
(Proteins 15%, lipids 8%, carbohydrates 2%, nucleic
acid 2%)
Carbohydrates - maltose (malt sugar) = glucose + glucose
- most abundant in nature among the other 3. Polysaccharide
macromolecules - made up of polymers or chains of many saccharide units.
- produced largely by green plants, algae, and some - starch = polymer of glucose
bacteria by photosynthesis (sugars, provide most of the - glycogen= polymer of glucose
energy used by cells, if not immediately needed for - inulin= polymer of fructose
photosynthesis, they are converted into glycogen or fat)
Monosaccharide
Functions - the simplest sugar units which follows the definition of
- Metabolic precursors of all other macromolecules polyhydroxyaldehyde or polyhydroxyketone
- Primary source of energy for humans and animals - colorless, crystalline solids
- Important component of cell walls and extracellular - very soluble in water because hydrogen bonding is
structures in plants, animals, and bacteria possible between their polar —OH groups and water
- Plays an important role in cell recognition - slightly soluble in ethanol and are insoluble in non-polar
solvents such as diethyl ether, dichloromethane, and
Definition benzene
- (Nutrition) substances that provide energy for various - Classification of Monosaccharide & Nomenclature
metabolic processes. For every one gram of glucose (a 1. Accord. to the number of carbon atoms present
carbohydrate that is converted to ATP), 4 kcal of energy is - prefix: tri-, tetr-, pent-, & hex- | suffix: -ose
produced. - ex. Triose, tetrose, pentose
- (Etymology) “hydrates of carbon” 2. Accord. to the type of carbonyl group present and the
- (Structure) are polyhydroxy aldehydes and ketones or number of C atoms
substances that yields these compounds upon hydrolysis. - Aldoses (CHO) = “aldo” + number of carbon + -ose
- ex. aldopentose, aldotriose, aldohexose
- Ketose (CO) = “keto” + number of carbon + -ose
- ex. ketotriose, ketotetrose, ketopentose
3. Haworth Structures
- represent the cyclic structures of monosaccharides as
*furanose ring – 5 membered ring monosaccharide
- often produced by aldopentoses and
ketohexoses
*pyranose ring – 6 membered ring monosaccharide
- often produced by aldohexoses
- Nomenclature:
a. indicate whether α- (alpha) or β- (beta)
b. indicate whether D- or L-
c. root name of monosaccharide = drop the –se ending
2. Hemiacetal/ Hemiketals d. type of ring: pyranose or furanose
- Reaction between alcohol and aldehydes or ketones - Name transitions from Haworth, to Hemi-acetal, to
- Cyclic hemiacetals reaction often occurs between the Fischer:
anomeric carbon (carbon containing the HC=O for aldoses Haworth Name : β-D-glucopyranose
or C=O for ketoses) and the OH of the penultimate carbon Hemi-Acetal Name : β-D-glucose
(second to the last carbon). Fischer Name : D-glucose
- The hemiacetal produced from D-monosaccharides - How to draw
occur in two forms called anomers: Determine the Fischer name from the given Haworth
*α- (alpha) if the OH of the anomeric carbon is at the name
right.
*β- (beta) if the OH of the anomeric carbon is at the left.
Derivatives of Monosaccharide
Sugar Acids
Assign OH groups to the carbons on the ring except for - formed by the oxidation of the aldehyde and/or primary
the two carbons nearest to oxygen based on the following: alcohol in aldoses into carboxylic acid groups
*if the OH is at the left in the Fischer structure = OH is
drawn upward in the Haworth ring
*if the OH is at the right in the Fischer structure = OH is
drawn downward in the Haworth ring (p. 31)
5. Amino Sugars
- Amino sugars are constituents of structures found in all
tissues, mostly on the surface of cells and in the spaces
between them, forming the substance that binds cells
together, membranes that envelope them and protective
layers that cover them.
- only occurs in carbons 2-4 - The surface of red blood cells contain glycoproteins
(sugar containing proteins) that determines the blood type
(has specific antigens and antibodies against other blood
types).
Disaccharide Sugars
1. Maltose
- a-D-glucopyranose + a-D-glucopyranose
- glycosidic linkage: a-(14)
- A product of the hydrolysis of starch and is eventually
broken down into glucose to be absorbed in the body.
- Known as “malt sugar” since it is found in wheat and
barley from which malt extract is produced commercially.
Disaccharides
- a group of carbohydrates that are composed of two
monosaccharides bonded together
- The bond between the two monosaccharides is called
glycosidic bond usually in carbon 1-4
- formed through condensation (combining small units
together) dehydration (removal of water) reactions.
2. Lactose
- b-D-galactopyranose + a-D-glucopyranose
- glycosidic linkage: b-(14)
- Known as “milk sugar”. It is found in milk and milk
products.
- Synthesized by lactating mammary gland
- Milk sugar (lac-milk)
- Enzyme – lactase and lactose intolerance
- Least sweet sugar – 16% of sucrose
- Possesses one potential aldehyde group
* reducing sugar
* forms osazone crystals
- Lactose intolerance
* A glass of milk often contains 11g of lactose
* In order for lactose to be absorbed, it should be broken
down into glucose and galactose by the enzyme lactase in
the small intestine.
* For those with lactose intolerance, the body is unable to
produce sufficient amount of lactase to break down
lactose
* When the undigested lactose reaches the large intestine,
lactose undergo fermentation which produces CO2 that
leads to an upset stomach
* A digestive disorder caused by the inability to digest
lactose
6. Fructose (Monosaccharide)
* symptoms: bloating, diarrhea, abdominal cramps
- Latin word for fruit — "fructus"
*diagnosis: oral tolerance test and/or measurement of H2
- Found in fruit juices, honey
gas in breath
- Released by the hydrolysis of inulin
3. Glucose (Monosaccharide)
- Main nutritional source of energy for the spermatozoa
- Found in fruits, fruit juices, hydrolysis of starch, maltose
and is found in the seminal fluid
and lactose.
- Can be converted to glucose in the liver
- Body sugar and the principal one used by the tissues
- It is the sweetest sugar
- Excess in the blood is called hyperglycemia and
- Lack of enzymes of metabolism can lead to essential
presence in urine (glucosuria) indicates diabetes mellitus
fructosuria
- Cataract due to sorbitol
4. Galactose (Monosaccharide)
Reducing Disaccharide
- Greek word for milk--"galact", found as a component of
- Disaccharides with a free anomeric Carbon which was
lactose in milk
not used in forming the glycosidic bond.
- Formed by the hydrolysis of lactose
- Synthesized in the lactating mammary gland
- Constituent of glycolipids and glycoproteins
- Can be converted to glucose in the liver
- Accumulation can lead to galactosemia and cataract
(galactitol)
5. Sucrose
- a-D-glucopyranose + b-D-fructofuranose
- glycosidic linkage: a-(12)
- non-reducing sugar because there is no free anomeric
carbon that can form other glycosidic bond
Polysaccharides according to their function
1. Storage Polysaccharide
- These polysaccharides is the storage form of
monosaccharides and is used as energy source for cells.
*Starch (homoglycan)
- contains a-D-glucose units only which gives rise to a
chain that folds in a helical form
- energy reserve of plants which are stored in granules
within cells
- most abundant dietary carbohydrate in cereals, potatoes,
legumes and other vegetables.
Dental carries - Used as thickening agent in cooking
- Dental caries or cavities refers to the destruction of the - composed of amylose and amylopectin
enamel surface of teeth caused by acids resulting from - Amylose is made up of unbranched chains of up to 4000
bacterial breakdown of sugars in the mouth. D-glucose units joined by α(1-4) glycosidic bonds;
unbranched and accounts for 15-20% of starch
Polysaccharide (glycans) - Amylopectin contains chains up to 10,000 D-glucose
- are carbohydrates that are made up of many saccharide units joined by α(1-4)glycosidic bonds; at branch points,
units. new chains of 24 to 30 units are started by α(1-6)
- made up of chains or polymers of saccharide units. glycosidic bonds; branched and accounts for 80-85% of
- usually made up of more than 10 saccharide units. starch that has higher molecular weight than amylose due
- carbohydrates with 3 – 9 saccharide units are called to branching
oligosaccharide. *Glycogen (homoglycan)
- the monosaccharides that make up polysaccharides are - has a structure that is similar to amylopectin but is much
bonded together by glycosidic bonds in nature occur as more branched
polysaccharides. - energy reserve of animals which is deposited in the liver.
- most abundant type of carbohydrates - also abundant in muscle tissues where it is more
immediately available for energy release.
Classification Of Polysaccharides - a branched polysaccharide of approximately 106 glucose
A. According to Composition units joined by α(1-4) and α(1-6) glycosidic bonds.
- polysaccharides may be classified based on its repeating *Dextrin (homoglycan)
units. - intermediate product of the hydrolysis of starch.
1.Homoglycan – made up of only one kind of - Used as adhesives, glue and binders. Also used as
monosaccharide as its repeating unit. mucilages at the back of postage stamps.
a. Hexosans – polysaccharides that yield hexoses upon - Mixture of linear α(1-4) linked D-glucose polymers
hydrolysis starting with an α(1–6) bond.
i. Glucans – polysaccharides made up of glucose units. *Dextran (homoglycan)
ii. Fructans – polysaccharides of fructose. - Used as blood extenders to increase the volume of
iii. Galactans – polysaccharides of galactose. circulating blood.
b. Pentosans – polysaccharides that yield pentoses upon - Found in dental plaque
hydrolysis. - A branched polysaccharide made of many glucose units
2. Heteroglycan – made up of two or more different kinds joined by α(1-4) linkages with branches bonded with
of monosaccharide or sugar derivatives as its repeating α(1-6) linkages.
unit. *Inulin (homoglycan)
B. According to Function - Energy reserve of plants containing tubers and bulbs like
- polysaccharides fulfill a wide variety of functions in onions and garlic.
living organisms. Hence, it is best to categorized
polysaccharides according to their function.
- Suitable for diabetics and helpful in managing blood - Agarose contains equal portions of D-galactose and 3,6-
sugar illness. anhydro-L-galactose. Agaropectin also contains D-
- Mainly compose of fructose units which are joined by galactose and 3,6-anhydro-L-galactose plus traces of ester
ß(2-1) glycosidic bonds sulfate and D-guluronic acid. The sugars are bonded with
2. Structural Polysaccharide alternating α(1-3) and ß(1-4) linkages.
- plays a role in providing shape, structure and outer *Peptidoglycan (heteroglycan)
covering of organisms - Found in the cell wall of bacteria and other prokaryotes.
*Cellulose (homoglycan) - made up of N-acetylglucosamine and N-acetylmuramic
- contains b-D-glucose units which gives rise to a long acid bonded by ß(1-4) linkages.
chain which can hydrogen bond with each other 3. Acidic Polysaccharide
- Found in the cell wall of plant cells thus, giving plant - contains carboxyl groups or sulfate esters that plays an
cells a rigid shape which enables them to sustain important role in connective tissues. They are also
tremendous weight. referred to as Glycosaminoglycans. They are commonly
- The disaccharide repeating unit is cellobiose which is bonded with a protein like collagen.
made up of ß-D-glucose units which are held together in a - contain disaccharide repeating unit comprising an amino
straight chain by ß(1-4) glycosidic bonds. sugar and at least one component with negative charge
*Chitin (homoglycan) due to the presence of carboxyl or sulfate groups
- has identitical structure as cellulose except that the *Hyaluronic acid (homoglycan)
monosaccharide unit is the glucose derivative N-acetyl-D- - contains alternating residue of N-acetyl-D-glucosamine
glucosamine and D-glucoronic acid with alternating ß(1-4) and ß(1-3)
- Found in the exoskeleton of arthropods (crustaceans and linkage
insects) where the chitinous structure is hardened by - Found in the synovial fluid in joints which acts as
calcium carbonate deposits. lubricant and shock absorber in joints.
-A linear molecule of N-acetyl glucosamine bonded by - Also found in the vitreous of eyes which keeps the retina
ß(1-4) linkages. in place.
*Alginic acid (heteroglycan) - Made up of N-acetyl glucosamine and glucuronic acid
- Structural polysaccharide of brown algae and seaweeds which are bonded by ß(1-3) linkages.
like kelp *Heparin (homoglycan)
- Used as thickener, emulsifier and stabilizer due to its - contains alternating residues of D-glucoronate-2-sulfate
ability to hold water and large molecules. and N-sulfo-D-glucosamine-6-sulfate with α(1-4) linkage
- A linear molecule of D-mannuronic acid joined by ß(1- - Serves as anticoagulant (prevents blood clotting) by
4) linkages. Some alginic acids contain L-guluronic acids forming a complex with thrombin, the protein responsible
in addition to D-mannuronic acids. for blood clotting.
*Carageenan (homoglycan) - Made up of N-acetyl glucosamine or N-acetyl
- Structural polysaccharide of red seaweeds galactosamnine bonded by α(1-3) or α(1-4) linkages.
- Can hold solids in suspension thus, it is used in food *Chondroitin sulfate (heteroglycan)
processing to make ice cream, cocoa milk, butter, yogurt - Helps in maintaining structural integrity of tissues
etc. It is also used in the manufacturing of cosmetics, - Widely used as dietary supplement for the treatment of
toothpastes and many others. osteoarthritis
- A linear polysaccharide consisting of: ß-D-galactose-4- - Unbranched polysaccharides containing two alternating
sulfate and 3,6-α-D-anhydrogalactose. The sugar residues monosaccharides: D-glucuronic acid and N-acetyl-D-
are linked with alternating α(1-3) and ß(1-4) linkages galactosamine which are bonded by ß(1-3) linkages.
*Agar (heteroglycan)
- The structural polysaccharide which occurs in red algae. Hydrolysis of Starch
- Used as a culture medium to study microorganisms. - can be hydrolyze by acid and enzymes
- It has lower sulfate content hence it has greater tendency - acid-hydrolysis f starch small fragments gradually
for gelling. - starchamylodextrinerythrodextrin
- Contains two fractions: agarose and agaropectin. achrodextrinmaltose
- enzymatic hydrolysis of starch is brought about by
amylase Dietary fiber
- 2 types of amylase: α-amylase (hydrolyzes internal - fiber is known as cellulose
glycosidic bond [endoglycosidae]) and ß-amylase - this normalizes bowel movement, maintain bowel health,
(hydrolyzes terminal glycosidic bond [exoglycosidase]) and lower cholesterol levels
Simple Lipids
Nomenclature of Triglycerides
1. Identical fatty acids
- use the prefix –tri
- change the –ic acid ending to –in.
Triglycerides (Triglycerols)
- an ester of glycerol with three fatty acids.
- most abundant type of lipid in the human body.
- concentrated primarily in special cells (adipocytes)
2. Three different fatty acids
- ester bonds with product of water
- 1st and 2nd fatty acid -ic to - o
- 3rd fatty acid - ic to - in
- change the –ic acid ending of the first and second fatty
acids to -o
- change the –ic acid ending of the third fatty acid to –in.