Carbohydrates Structure and Function

The Structure and
Function of Carbohydrates
LECTURE
LESSON OUTLINE
• Carbohydrates – Overview
– Functions
– Major Groups and Classification
• Carbohydrates Stereochemistry
– Fischer Projection
– Haworth Projection
– Chair Conformation
• Essential Carbohydrates
Carbohydrates – Overview
Carbohydrates – consist
of carbon, hydrogen, and
oxygen atoms and are
polyhydroxy aldehydes or
ketones or are
compounds that can be
broken down to form such
compounds.
Important Functions of Carbohydrates

• Providing energy through their oxidation
• Supplying carbon for the synthesis of cell components
• Serving as a stored form of chemical energy
• Forming a part of the structural elements of some cells and tissues
Classification of Carbohydrates
• Monosaccharide – simple carbohydrate most commonly consisting
of three to six carbon atoms
• Disaccharide – carbohydrate formed by the combination of two
monosaccharide units
• Oligosaccharide – any carbohydrate of from three to six units of
simple sugars (monosaccharides)
• Polysaccharide – carbohydrate formed by the combination of many
monosaccharide units
Carbohydrates Stereochemistry
Many carbohydrates exist as enantiomers

• Enantiomers – stereoisomers that are mirror images
Chiral – descriptive term for

compounds or objects that cannot
be superimposed on their mirror
image
Chiral carbon – carbon atom with
four different groups attached
Center carbon of glyceraldehyde is
chiral
Presence of a single chiral carbon gives rise to stereoisomerism

• If a carbon atom is attached to four different groups, it is chiral
– If any two groups are identical, it is not chiral
• Organic molecules can have more than one chiral carbon

• Maximum number of stereoisomers is 2n, where n is the number of
chiral carbon atoms
• 2
Compound with two chiral carbon atoms has 2 , or 4 stereoisomers
• 4
Compound with four chiral carbon atoms has 2 , or 16 stereoisomers
Fischer Projection – depict three-dimensional shapes for chiral

molecules, with the chiral carbon represented by the intersection of
two lines
• Fischer projections of carbohydrates have
the carbonyl (C=O) at or near the top
– C=O projects away from the viewer into the
plane of the paper in which it is drawn as is the
other vertical bond at the bottom of the image
• Hydroxyl group on the chiral carbon
farthest from the C=O group determines
whether the carbohydrate is D (—OH on
right) or L (—OH on left)
– Two horizontal bonds come toward the viewer
out of the plane of the paper in which they are
drawn
• Physical properties of D- and L- isomers are generally the same
• D- and L- enantiomers rotate polarized light in equal but opposite directions
• Levorotatory
– Enantiomer that rotates plane-polarized light to the left
– (−) enantiomer
• Dextrorotatory
– Enantiomer that rotates plane-polarized light to the right
– (+) enantiomer
• D and L designations do not represent dextrorotatory and levorotatory but only
the spatial relationship of a Fischer projection
• Only one stereoisomer is found in nature for carbohydrates and

amino acids even though they are chiral
– Two enantiomers are found in nature in some instances but are not found
together in the same biological system
– Examples
• Humans can only metabolize the D-isomers of monosaccharides
• Most animals are able to utilize only the L-isomers of amino acids to
synthesize proteins
Classification of Monosaccharides
Number of Carbon Atoms Sugar Class

3 Triose
4 Tetrose
5 Pentose
6 Hexose
Classification of Monosaccharides
• Most monosaccharides are aldoses
• Almost all natural monosaccharides belong to the D- series
• Half of stereoisomers are D- and the other half are L-
# of Carbon Name of # of Chiral # of # of D # of L
Atoms Sugar Class Carbon Atoms Stereoisomers Stereoisomers Stereoisomers
(n) (2n)
3 triose 1 2 1 1
4 tetrose 2 4 2 2
5 pentose 3 8 4 4
6 hexose 4 16 8 8
Physical Properties of Monosaccharides

• Most monosaccharides and disaccharides are called sugars
because they taste sweet
• All carbohydrates are solids at room temperature
• Monosaccharides are extremely water soluble
– Because of the many —OH groups forming hydrogen bonds with water
molecules
Sugar Relative Sweetness Type

Lactose 0.16 Disaccharide
Galactose 0.22 Monosaccharide
Maltose 0.32 Disaccharide
Xylose 0.40 Monosaccharide
Glucose 0.74 Monosaccharide
Sucrose 1.00 Disaccharide
Invert sugar 1.30 Mixture of glucose and fructose
Fructose 1.73 Monosaccharide
All monosaccharides with at least five carbon atoms exist

predominantly as cyclic hemiacetals and hemiketals
• Haworth structure – method of depicting three-dimensional
carbohydrate structures
• Open-chain structure is numbered starting at the end closest to the carbonyl
carbon atom
• Alcohol group on the carbon next to the last carbon atom adds to the carbonyl
group
• In the case of glucose, the alcohol group on carbon 5 adds to the aldehyde
group on carbon 1 and a pyranose ring forms
– Pyranose ring – Six-membered ring containing an oxygen atom
• In the case of fructose, the alcohol group on carbon 5 adds to the ketone group
on carbon 2 and a furanose forms
– Furanose ring – Five-membered ring containing an oxygen atom
• Former carbonyl carbon atom is now chiral and called the anomeric carbon
atom
Anomeric carbon: Acetal, ketal, hemiacetal, or hemiketal carbon atom giving rise
to two stereoisomers
• Two possible stereoisomers can be formed during cyclization

– α anomer – —OH on the anomeric carbon pointing down
– β anomer – —OH on the anomeric carbon pointing up

• Anomers: Stereoisomers that differ in the 3-D arrangement of groups at the carbon of an acetal, ketal, hemiacetal, or hemiketal group
Rules for Drawing Haworth

Structures
1. Draw the ring with its oxygen to
the back
2. Put the anomeric carbon on the
right side of the ring
3. Envision the ring as planar with
groups pointing up or down
4. The terminal —CH2OH group is
always shown above the ring for
D-monosaccharides
Chair Conformation
• For pyranoses, the six-membered ring is more accurately
represented as a chair conformation.
-in both a Haworth projection and a chair conformation, the

orientations of groups on carbon 1-5 of β-D-glucopyranose are up,
down, up, down and up.
In organic chemistry, we can represent certain compounds in

different ways structurally. Compounds which are 6-membered rings
or substituted 6-membered rings can be represented in two ways-
chair conformation and boat conformation.
In the chair conformation, the 2nd, 3rd, 5th and 6th carbon atoms lie
on one plane whereas the 1st carbon is above the plane and 4th
carbon is below the plane.
In the boat conformation, 1st, 2nd, 4th and 5th carbons are in one
plane while the 3rd and 6th carbons are bent in the same plane
outside of the plane.
Converting Haworth
Projection to Chair
Conformation
Essential Carbohydrates
Important Monosaccharides
A. Ribose and Deoxyribose
– Are pentoses
– Used in the synthesis of nucleic
acids (DNA and RNA), substances
essential in protein synthesis and
the transfer of genetic material
– Ribose forms the long chains that
make up RNA
– Deoxyribose forms the long chains
of DNA
B. Glucose
– Hexose is the most nutritionally
important monosaccharide
– Called dextrose or blood sugar
– Final form to which other sugars
absorbed into the body are converted
in the liver
– Used as a sweetener in confections
and other foods
C. Galactose
– Hexose with a structure similar to
glucose
– Component of lactose (milk sugar)
– Component of substances present in
nerve tissue
– Also known as “brain sugar”
D. Fructose
– Most important ketohexose
– Sweetest monosaccharide
– Called fruit sugar
– Present in honey in a 1:1 ratio with
glucose
– Abundant in corn syrup
Glycoside
• General name for a carbohydrate containing an acetal or ketal group
• Formed when cyclic monosaccharides (hemiacetals and hemiketals) react with
alcohols in the presence of acid
Glycoside
• Glycosidic linkage – New carbon–oxygen–carbon linkage that joins the
components of the glycoside to the ring
• Glycosides do not exhibit open-chain forms and thus are not reducing sugars
Disaccharides
• Two monosaccharide units linked together by acetal or ketal (glycosidic)
linkages
– Glycosidic linkage is identified by:
• Numbers associated with the carbon atoms joined together by the linkage
• Configuration of the linkage for any anomeric carbon atom joined by the linkage
Important Disaccharides
A. Maltose
– Called malt sugar
– Contains two glucose units joined by (1→4) glycosidic linkage
– Found in germinating grain
– Formed during the digestion of starch to glucose
– Reducing sugar since it contains a hemiacetal group
– Forms two molecules of D-glucose on hydrolysis
B. Lactose
– Called milk sugar (5% of cow milk and 7% of human milk by weight)
– Composed of galactose and glucose units joined by β(1→4) glycosidic linkage
– Reducing sugar as it contains a hemiacetal group
C. Sucrose
– Common household sugar
– Composed of fructose and glucose units
joined by α1→β2 glycosidic linkage
– Found in the juices of many plants
(especially sugar cane and sugar beets)
– Not a reducing sugar
– Hydrolyzed to produce invert sugar
• Invert sugar – Mixture of equal amounts of
glucose and fructose
Oligosaccharides
• Carbohydrates that contain three or more monosaccharides units
• May contain any sugar monomer, but fructooligosaccharides (e.g.,
oligofructose) and galactooligosaccharides are mostly researched.
• Some oligosaccharides get absorbed in the small intestine after
getting hydrolsed, for example, maltotriose.
Oligosaccharides
• Examples of Oligosaccharides
– Raffinose – a trisaccharide having
formula C18H32O16 is formed with three
sugar units – fructose, glucose, and
galactose.
– It produces D-galactose and sucrose
when it gets hydrolyzed with α-
galactosidase enzyme.
– It is found in legumes, beetroots,
cabbage, cottonseed, broccoli, etc.
Oligosaccharides
– Fructooligosaccharides – plant-derived
oligosaccharides
– These are short chains of fructose
residues which are common in plants
(banana, onion, wheat, barley, etc.).
– They are commercially used as food
additives to enhance color and
texture, and also as artificial
sweeteners.
Oligosaccharides
– Galactooligosaccharides – made up of
galactose molecules
– They are present in breast milk.
– They are derived from lactose. 2′-
fucosyllactose, i.e., a trisaccharide
composed of fucose, galactose, and
glucose accounts for 30% of all
human milk oligosaccharides.
Glucosamines
• an amino sugar and a
prominent precursor in the
biochemical synthesis of
glycosylated proteins and
lipids.
• one of the most abundant
monosaccharides.
Sugar Molecules to help Blood Typing
Polysaccharides
• Condensation polymers containing thousands of units
• Not water soluble but hydroxy groups become hydrated individually
when exposed to water
• Can form thick colloidal dispersions when heated in water
• Example – Starch
– Used as a thickener in sauces, gravies, pie fillings, and other food
preparations
Property Monosaccharides and Polysaccharides

Disaccharides
Molecular weight Low Very high
Taste Sweet Tasteless
Solubility in water Soluble Insoluble or form
colloidal
dispersions
Size of particles Pass through a membrane Do not pass through a
membrane
Test with Cu2+ for Positive (except for sucrose) Negative
reducing sugars
Important Polysaccharides
A. Starch
• Polymer consisting of D-glucose units
• Major storage form of D-glucose in plants
– Amylose and amylopectin can be isolated from plants
– Structure of amylose - Unbranched chain (10-20%), which is composed of 1000–2000
glucose units with α(1→4) glycosidic linkages
A. Starch
– Amylose and amylopectin can be isolated from plants
– Structure of amylopectin - Branched chain (80-90%) with (1
→→4) and (1→ 6) glycosidic
linkages
B. Glycogen
– Called animal starch
– Polymer of glucose units
– Used by animals to store glucose,
especially in the liver and muscles
– Structurally similar to amylopectin
with α(1→4) and α(1→6) linkages but
more highly branched
C. Cellulose
– Polymer of D-glucose units
– Most important structural polysaccharide
– Most abundant organic compound on Earth
– Found in plant cell walls
– Linear polymer like amylose but has β(1→4)
glycosidic linkages
– Not easily digested
– Constituent of dietary fiber that aids in
intestine contraction
D. Hyaluronic Acid
– an anionic, non-sulfated glycosaminoglycan distributed widely throughout
connective, epithelial, and neural tissues.
– It acts as a cushion and lubricant in the joints and other tissues.
E. Heparin
• naturally occurring glycosaminoglycan.
• It is used to decrease the clotting ability of the blood and help prevent harmful
clots from forming in blood vessels.

Carbohydrates Structure and Function

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Carbohydrates Structure and Function

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The Structure and

Important Functions of Carbohydrates

Many carbohydrates exist as enantiomers

Chiral – descriptive term for

Presence of a single chiral carbon gives rise to stereoisomerism

• Organic molecules can have more than one chiral carbon

Fischer Projection – depict three-dimensional shapes for chiral

• Only one stereoisomer is found in nature for carbohydrates and

Number of Carbon Atoms Sugar Class

Physical Properties of Monosaccharides

Sugar Relative Sweetness Type

All monosaccharides with at least five carbon atoms exist

• Two possible stereoisomers can be formed during cyclization

– β anomer – —OH on the anomeric carbon pointing up

Rules for Drawing Haworth

-in both a Haworth projection and a chair conformation, the

In organic chemistry, we can represent certain compounds in

Property Monosaccharides and Polysaccharides

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