VIETNAMATIONAL UNIVERSITY HCMC
INTERNATIONAL UNIVERSITY
BTBC209IU
Biochemistry 1
Nguyen Kim Truc (PhD)
Office: A1.705
Email: nktruc@hcmiu.edu.vn
AY 2019-2020, semester 2
Biomolecules
Biomolecules
Biomolecules
Carbohydrates
Introduction to Carbohydrates
What are the structure, chemistry, and biological functions of
carbohydrates?
• Naming carbohydrates
• Structure and chemistry of monosaccharides, oligosaccharides,
polysaccharides
• Functions of carbohydrates in nature
How are carbohydrates named?
Carbohydrates are hydrates of carbon
with the general formula (CH2O)n
Carbohydrates are classified in three groups:
• Monosaccharides (simple sugars) - cannot be broken down into
simpler sugars under mild conditions
• Oligosaccharides (oligo = "a few“) - usually 2 to 10 simple sugar
residues
• Polysaccharides - polymers of the simple sugars
Structure and Chemistry of
Monosaccharides
• Aldoses and ketoses contain aldehyde and ketone functions,
respectively
• Triose, tetrose, etc. denotes number of carbons
• Chiral molecules usually contain at least one carbon atom with four
nonidentical substituents. Any molecule that contains a chiral center
will be chiral.
Structure and Chemistry of
Monosaccharides
An aldose is a monosaccharide (a
simple sugar) with a carbon
backbone chain with a carbonyl
group on the endmost carbon
atom, making it an aldehyde,
and hydroxyl groups connected
to all the other carbon atoms.
Aldoses can be distinguished
from ketoses, which have the
carbonyl group away from the
end of the molecule, and are
therefore ketones.
The Aldoses
The Ketoses
Stereochemistry Review
• D,L designation refers to the configuration of the highest-
numbered asymmetric center
Stereochemistry Review
• D,L designation refers to the configuration of the highest-numbered
asymmetric center
• D,L do not specify the sign of rotation of plane-polarized light
• D-sugars predominate in nature
• Dextrorotatory: clockwise rotation of incident light
• Levorotatory: counterclockwise rotation of incident light
• If a chiral molecule is dextrorotary, its enantiomer (geometric
mirror image) will be levorotary, and vice versa
Read text on page 204-209 in text book carefully
(PDF file of this part had been posted on blackboard)
Stereochemistry Review
A standard measure of the degree to which a compound is
dextrorotary or levorotary is the quantity [α], known as
the specific rotation.
α = observed rotation (in degrees),
c = concentration of the solution of
an enantiomer (in g/ml),
l = length of the polarimeter tube
(in decimeters).
Application: a tool of great importance to calculate the
concentration of sugar syrups in bulk in industry. For a pure
substance in solution, if the color and path length are fixed and the
specific rotation is known, the observed rotation can be used to
calculate the concentration.
Digital polarimeter
Digital polarimeter Polarimeter cell
Optical rotation of sugar and their applications
Stereochemistry Review
• Enantiomers: Stereoisomers that are nonsuperimposable mirror
images of each other
Stereochemistry Review
• Enantiomers: Stereoisomers that are nonsuperimposable mirror
images of each other
Stereochemistry Review
• Enantiomers: Stereoisomers that are nonsuperimposable mirror
images of each other
• Diastereomers: Pairs of isomers that have opposite configurations
at one or more chiral centers but are NOT mirror images
Stereochemistry Review
• Enantiomers: Stereoisomers that are nonsuperimposable mirror
images of each other
• Diastereomers: Pairs of isomers that have opposite configurations
at one or more chiral centers but are NOT mirror images
• Epimers: Two sugars that differ in configuration at only one chiral
center
Cyclic monosaccharide structures and
anomeric forms
• Glucose (an aldose) can cyclize to form a cyclic hemiacetal
• Fructose (a ketose) can cyclize to form a cyclic hemiketal
• When hemiacetals and hemiketals are formed, the carbonyl
carbon atom becomes an asymmetric center
• Isomers of monosaccharides that differ only in their configuration
about that asymmetric carbon are called anomers
• Cyclic form of glucose is a pyranose
• Cyclic form of fructose is a furanose
Hemiacetal formation
Hemiacetal formation
Hemiacetal formation
Hemiketal formation
Hemiketal formation
Hemiketal formation
Sugar cyclize in two ways
Sugar cyclize in two ways
Anomers
•Isomers of monosaccharides that differ only in their configuration
about the asymmetric carbon derived from the carbonyl C are called
anomers
Anomers
•Isomers of monosaccharides that differ only in their configuration
about the asymmetric carbon derived from the carbonyl C are called
anomers
•When the hydroxyl group at the anomeric carbon is on the same side
of a Fischer projection as the oxygen atom at the highest numbered
asymmetric carbon, the configuration at the anomeric carbon is α
A simpler rule:
• For D-sugars, alpha has OH down, beta has OH up (In the customary
Haworth drawing)
• For L-sugars, the reverse is true
Anomers
•When the hydroxyl group at the anomeric carbon is on the same side
of a Fischer projection as the oxygen atom at the highest numbered
asymmetric carbon, the configuration at the anomeric carbon is α
Anomers
A simpler rule:
• For D-sugars, alpha has OH down, beta has OH up (In the customary
Haworth drawing)
• For L-sugars, the reverse is true
Chair and boat conformation
(a) Chair and boat conformations of a pyranose sugar.
(b) Two possible chair conformations of β-D-glucose.
Note the axial and equatorial substituents.
Chair and boat conformation
Step 1 Step 2 Step 3
Chair and boat conformation
Step 4
Up tip
down tip
Chair and boat conformation
Step 5
Alternate your axial substituents up and down all the way
around your cyclohexane
Every carbon on the chair conformation has 1 substituent axial and
the other equatorial. If axial is up equatorial is down, if equatorial is
up then axial is down.
Chair and boat conformation
Step 6
Adding substituents to your chair
Monosaccharides derivative forms
• A variety of chemical and enzymatic reactions produce
derivatives of the simple sugars
• Some of the most common are:
Sugar acids
Sugar alcohols
Deoxy sugars
Sugar esters
Amino sugars
Acetals, ketals, and glycosides
Q&A
