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2.2 Carbohydrate
Chemistry
Metabolism
[Biochemistry] 2.2 Carbohydrate
Chemistry
and Metabolism
Dr. and
Donato
Dr. Donato
CHO Chemistry
STEREOISOMERS compounds with the same formula
and attachment of atoms but with different arrangements of
the atoms in space.
CHO Chemistry
Monosaccharides
Disaccharides
Polysaccharides
Other CHO Polymers
CHO Digestion and Absorption
OBJECTIVES
At the end of the lecture, the student should be able to:
1. Discuss: Overview of CHO polymers.
2. Illustrate the structure of glucose and other biologically
important sugars.
3. Recognize features of carbohydrates.
4. Discuss the features of glycosidic bonds.
5. Discuss: CHO breakdown from dietary sources.
References:
1. Devlin, T.M. Textbook of Biochemistry, 7th edition. 2011.
2. Abainza, et al. Carbohydrate Chemistry and Absorption.
Biochemistry Transcription. 2011.
3. Berg, et al. Biochemistry, 5th edition.
4. Cox, et al. Lehninger Principles of Biochemistry, 5th
edition, 2008.
5. Smith, et al. Marks Basic Medical Biochemistry: A
Clinical Approach, 2nd edition.
6. Granner, et al. Harpers Illustrated Biochemistry, 26th
edition, 2003.
7. Donato, C. Carbohydrate Chemistry and Metabolism.
Lecture. UERM Anatomy Amphitheater. July 25, 2013
Legend: Italicized quoted from the lecturer; bold
emphasis, or from references
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D-Galactose
- An aldohexose.
- Differs in the position of OH at C4.
- C4 is the non-reducing end.
- Can be changed to glucose in the liver and
metabolized.
- Synthesized in the mammary glands to make the
lactose of milk.
- A constituent of glycolipids and glycoproteins.
D-Mannose
- An aldohexose
- Differs in the OH configuration at C2.
- A constituent of many glycoproteins.
Figure 3: D-glucose in Haworth projection. The position of the OH group
dictates whether it is or .
MONOSACCHARIDES
MONOSACCHARIDES simple sugars; carbohydrates that
cannot be hydrolyzed into simpler compounds.
D-Glucose
- An aldohexose.
- Has the empirical formula (C6H12O6)
- In biological solutions, pyran-D is the most stable
form of glucose (pictured below)
- Biomedically the most important monosaccharide.
- The sugar of the body. The sugar carried by the
blood, and the principal one used by tissues.
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DISACCHARIDES
DISACCHARIDES formed when the anomeric carbon of
one sugar molecule interacts with one of several hydroxyl
groups in the other sugar molecule.
GLYCOSIDIC BONDS
o Primary structural linkage in all polymers of
monosaccharides.
o An acetal linkage in which the anomeric carbon of a
sugar is condensed with an alcohol, an amine, or a
thiol (R-O-C-O-R).
o The carbon in the acetal has a fixed or position.
D-Ribose
- An aldopentose.
- Found in RNA.
- Structural elements of nucleic acids and coenzymes,
e.g. ATP, NAD, NADP, flavoproteins.
- Ribose phosphates are intermediates in the HMP
Shunt.
MALTOSE
- -D-glucopyranosyl-(1 4)--Dglucopyranose.(Lehninger 5/E, pg. 243)
- Composed of two -D-glucose residues linked by an
1,4-glycosidic bond.
- Present in malt, obtained from corn or grain that is
used in malted milk and brewing
- Can be broken down by the enzyme maltase.
- is a reducing sugar because there is a free hydroxyl
group on the anomeric carbon of monosaccharide B.
It can bond again to glucose.
- linear
D-Deoxyribose
- Reduced form of Ribose; difference is in C2.
- C2 contains H below the ring
- Found in DNA
Figure 10: Formation of Maltose between two Glucose residues. Note that
the reaction involves loss of water.
ISOMALTOSE
- -D-glucopyranpsyl-(16)--D-glucopyranose.
- Two -D-glucose residues bonded covalently with
an 1,6-glycosidic bond.
- Can be broken down by sucrase-isomaltase
complex.
- branched
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LACTOSE
- -D-galactopyranosyl-(14)--D-glucopyranose
(Lehninger 5/E, pg. 244)
- A -D-galactose and -D-Glucose bonded
covalently with a 1,4-glycosidic bond.
- Major carbohydrate in milk
- Synthesized in lactating mammary glands (females
only)
- Can be broken down by the enzyme lactase or galactosidase. (inducible enzyme)
- Enzyme depletes as the individual ages if lactose is
not maintained in the diet. This leads to lactose
intoleranceosmotic diarrhea and flatulence upon
ingestion of lactose-rich foods.
- There is now an exogenous lactase preparation to
counter lactose intolerance.
ENZYME
DEFICIENCY
lactase
Gal1PO4 Uridyl
Transferase (inherited
disease)
TREATMENT
avoid products
containing too much
milk, consumption of
milk in small amounts
remove galactose
and lactose from
the diet
SUCROSE
- -D-glucopyranosyl-(12)--D-fructofuranoside
- Formed by linkage of C1 of -D-Glucose and C2 of
-D-Fructose with a 1, 2-glycosidic bond.
- The sweetest sugar; synthesized only in plants.
- Commonly known as table sugar; obtained from
cane or beet, some fruits and vegetables
- Can be broken down by Sucrase.
- Note that the anomeric carbons of glucose and
fructose are both involved in the glycosidic bond;
hence, sucrose has no free hydroxyl group on the
anomeric carbon. Sucrose is thusly a non-reducing
sugar and will not react with Benedict solution.
POLYSACCHARIDES
POLYSACCHARIDES large polymer oligosaccharides
formed by the linkage of multiple monosaccharides. They
play vital roles in energy storage and in maintaining the
structural integrity of an organism.
Figure 14: Starch structure. (A) Amylose, showing helical coil structure. (B)
Amylopectin, showing 1,6-glycosidic linkage.
CELLULOSE
- Polysaccharide that serves a structural role; found in
the cell walls of plants
- Formed by 1,4-glycosidic bonds.
- there is no enzyme for cellulose in the human body;
insoluble
GLYCOPROTEINS
- Structure: CHO + Serine, Threonine, Asparagine
- Found in the cell membrane, extracellular matrix and
in the blood.
- Components of antibodies and hormones
- e.g. Antigens on the cell membrane for ABO blood
typing.
GLYCOGEN
- Main storage of glucose in animal cells
- It is composed of one 1,6-glycosidic bonds for
every 8-12 1,4-glycosidic bond.
- More highly branched and compact than
amylopectin.
Figure 17: Diagram showing the carbohydrate chains that determine the
ABO blood group.
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GLUT 1:
o High-affinity glucose transport system
o Found in all cells; more expressed in cell types with
barrier functions.
o Glucose transporter of RBCs.
o Exhibits specificity for glucose and related Dhexoses.
GLUT 2:
o High-capacity, low-affinity transporter
o Found in liver, pancreatic cells, small intestine
and kidneys; contraluminal side of enterocytes.
o In liver, facilitiates outward transport of glucose
when liver glycogen is broken down to meet
physiological needs.
o Is signaled by insulin for storage as glycogen or
conversion to fat.
o All three monosaccharides (glucose, galactose,
fructose) are transported from the intestinal mucosal
cell into the portal circulation.
GLUT 3:
o High-affinity glucose transport system
o Found in the brain (neurons), kidneys, placenta
o Major transporter in the CNS
o Transport D-sugars and glycerol.
GLUT 4:
o High-affinity, insulin-dependent transporter
o Found in cardiac and skeletal muscle, adipose
tissue
o When not activated by insulin, GLUT4 are contained
in vesicles near the membrane of the cell.
o Once insulin binds to its receptor a signalling pathway
initiates the migration of GLUT 4 to the cell
membrane, leading to an increase in GLUT4
transpoters.
o Can also increase in amount with exercise.
o Transport D-sugars and glycerol
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GLUT 5:
o Fructose transporter
o Found in small intestine. Testes and sperm cells also
prefer fructose.
o High-fructose dietary sources are very high in calories
because it can be oxidized on its own and it has its
own transporter.
COMPETENCIES:
1.) Given a normal newborn, identify biochemical pathways
or processes of carbohydrates that are involved to
achieve normal growth and development.
Glycolysis - the oxidation metabolism of glucose
molecules to obtain ATP and pyruvate
o Pyruvate from glycolysis enters the Krebs
cycle, also known as the citric acid cycle, in
aerobic organisms after moving through
pyruvate dehydrogenase complex.
The pentose phosphate pathway, which acts in
the conversion of hexoses into pentoses and in
NADPH regeneration.
Glycogenesis - the conversion of excess glucose
into glycogen as a cellular storage mechanism; this
prevents excessive osmotic pressure buildup inside
the cell
Glycogenolysis - the breakdown of glycogen into
glucose, which provides a glucose supply for
glucose-dependent tissues.
Gluconeogenesis - de novo synthesis of glucose
molecules from simple organic compounds. An
example in humans is the conversion of a few
amino acids in cellular protein to glucose.
DIETARY CARBOHYDRATES
Carbohydrate
Source
Fructose
Fruits, honey
Glucose
Fruits, honey, grape
Amylopectin
Potatoes, rice, corn, bread
Amylose
Potatoes, rice, corn, bread
Sucrose
Table sugar, desserts
Trehalose
Young mushrooms
Lactose
Milk, milk products
Raffinose
Leguminous seeds
CLINICAL CORRELATION
DISACCHARIDASE DEFICIENCY
Present in one or more enzymes due to genetic
defects, physiological decline with age or injuries to
mucosa.
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