3 1carbohydrate

Carbohydrates
2019.3.25
Outlines
• Classes of carbohydrates
• Structures (straight-chain and cyclic) of monosaccharide:
glucose, fructose, ribose
• Derivatives of hexose
• Common disaccharides
• Explain: reducing sugar, glycosidic bond, epimer

Functions
• Carbohydrates are the most abundant biomolecules on earth.

• Sugar and starch are a dietary staple and provide energy for cells.
• Structural component: glycans are component of cell walls of
bacteria and plants.
• Other carbohydrate polymers lubricate skeletal joints and
participate in recognition and adhesion between cells.
Component
• Carbohydrates are polyhydroxy aldehydes or ketones, or

substances that yield such compounds on hydrolysis.
• Many, but not all, carbohydrates have the empirical formula
(CH2O)n; Some contain nitrogen, phosphorus, or sulfur.
Classes of carbohydrates
• There are three major classes of carbohydrates:

monosaccharides, oligosaccharides, and polysaccharides.
• Monosaccharides consist of a single polyhydroxy aldehyde or
ketone unit. The most abundant monosaccharide in nature is
the six-carbon sugar D-glucose.
• Oligosaccharides consist of short chains of monosaccharide
units, or residues, joined by characteristic linkages called
glycosidic bonds. The most abundant are the disaccharides.
• The polysaccharides are sugar polymers containing more than
20 or so monosaccharide units; some have hundreds or
thousands of units. Eg. Glycogen, starch, cellulose.
Monosaccharides
• Monosaccharide is either an aldose (the carbonyl group is at

the end of the carbon chain) or a ketose (the carbonyl group is
at any other position)
• Monosaccharides with four, five, six, and seven carbon atoms
in their backbones are called, respectively, tetroses, pentoses,
hexoses, and heptoses.
Aldose
Ketose
Monosaccharides Have Asymmetric Centers
The simplest aldose, glyceraldehyde, contains one chiral center

(the middle carbon atom) and therefore has two different optical
isomers, or enantiomers.
Monosaccharides Have Asymmetric Centers
What about dihydroxyacetone? Does it contain chiral center?

Fischer projection formulas
To represent three-dimensional sugar structures on paper, we

often use Fischer projection formulas. In Fischer projection
formulas, horizontal bonds project out of the plane of the paper,
toward the reader; vertical bonds project behind the plane of
the paper, away from the reader.
Hexoses
• The hexoses, which include the aldohexose D-glucose and the

ketohexose D-fructose, are the most common
monosaccharides in nature.
In the USA corn (more precisely: corn
syrup) is used as glucose source for the
production of isoglucose, which is a
mixture of glucose and fructose, since
fructose has a higher sweetening
power — with same physiological
calorific value of 374 kilocalories per
100 g. The annual world production of
isoglucose is eight million tons (as of
2011. When made from corn syrup, the
final product is high fructose corn syrup
(HFCS).
Most countries, including Mexico, use
sucrose, or table sugar, in soft drinks.
In the U.S., soft drinks, including
Coca-Cola, are typically made with
HFCS. Some Americans seek out
drinks such as Mexican Coca-Cola in
ethnic groceries because they prefer
the taste over that of HFCS-
sweetened Coca-Cola
Sucrose is common table sugar. It

is a disaccharide, a molecule
composed of two
monosaccharides: glucose and
fructose.
Ribose
• The aldopentoses D-ribose and 2-deoxy-D-ribose are

components of nucleotides and nucleic acids
ATP
Monosaccharides Have Cyclic Structures
• In aqueous solution, monosaccharides with five or more
carbon atoms in the backbone occur predominantly as cyclic
(ring) structures.
• The formation of these ring structures is the result of a
general reaction between alcohols and aldehydes or ketones
to form derivatives called hemiacetals or hemiketals.
Monosaccharides Have Cyclic Structures
Isomeric forms of
monosaccharides that
differ only in their
configuration about the
hemiacetal or hemiketal
carbon atom are called
anomers. The hemiacetal
(or carbonyl) carbon atom
is called the anomeric
carbon.
Mutarotation:
interconversion of the two
anomers.
Haworth perspective formulas
Pyranose (six-membered ring) and furanose (five-membered ring)
Further away from us

Near us
Two conformations of pyranose
Epimers
Two sugars that differ only in the configuration around one

carbon atom are called epimers; D-glucose and D-mannose,
which differ only in the stereochemistry at C-2, are epimers, as
are D-glucose and D-galactose (which differ at C-4)
Organisms Contain a Variety of Hexose Derivatives
• sugar derivatives: a hydroxyl group in the parent compound is

replaced with another substituent, or a carbon atom is
oxidized to a carboxyl group.
• Glucosamine is an amino sugar and a prominent precursor in
the biochemical synthesis of glycosylated proteins and lipids.
Glucosamine is part of the structure of the polysaccharides,
chitosan, and chitin.
• The amino group can be condensed with acetic acid, as in N-

acetylglucosamine. This glucosamine derivative is part of
many structural polymers, including those of the bacterial cell
wall.
Oxidation of the carbonyl (aldehyde) carbon of glucose to the

carboxyl level produces gluconic acid; other aldoses yield other
aldonic acids. Oxidation of the carbon at the other end of the
carbon chain—C-6—forms the corresponding uronic acid.
Monosaccharides Are Reducing Agents
Monosaccharides can be oxidized by relatively mild oxidizing

agents such as cupric (Cu2+) ion. The carbonyl carbon is oxidized
to a carboxyl group. Glucose and other sugars capable of
reducing cupric ion are called reducing sugars.
This test was used to detect and measure elevated glucose levels
in blood and urine in the diagnosis of diabetes mellitus.
(Fehling’s reaction)
Disaccharides Contain a Glycosidic Bond
• Disaccharides : maltose,
lactose, and sucrose.
• Two monosaccharides join
covalently by an O-glycosidic
bond, which is formed when a
hydroxyl group of one sugar
reacts with the anomeric
carbon of the other.
• Disaccharides can be
hydrolyzed to yield their free
monosaccharide components
by boiling with dilute acid.
Disaccharides Contain a Glycosidic Bond
Component of milk
Table sugar: Made by

plants, not animals
Summary
• Sugars (also called saccharides) are compounds containing an
aldehyde or ketone group and two or more hydroxyl groups.
• Monosaccharides generally contain several chiral carbons and
exist in a variety of stereochemical forms, represented on
paper as Fischer projections. Epimers are sugars that differ in
configuration at only one carbon atom.
• Monosaccharides commonly form internal hemiacetals or
hemiketals, creating a cyclic structure; this can be represented
as a Haworth perspective formula. The carbon atom originally
found in the aldehyde or ketone group (the anomeric carbon)
can assume either of two configurations, alfa and beta, which
are interconvertible by mutarotation. In the linear form, the
anomeric carbon is easily oxidized.
Summary
• A hydroxyl group of one monosaccharide can add to the

anomeric carbon of a second monosaccharide to form an
acetal. In this disaccharide, the glycosidic bond protects the
anomeric carbon from oxidation.
• Oligosaccharides are short polymers of several
monosaccharides joined by glycosidic bonds. At one end of
the chain, the reducing end, is a monosaccharide unit with its
anomeric carbon not involved in a glycosidic bond.

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Carbohydrates

• Explain: reducing sugar, glycosidic bond, epimer

• Carbohydrates are the most abundant biomolecules on earth.

• Carbohydrates are polyhydroxy aldehydes or ketones, or

• There are three major classes of carbohydrates:

• Monosaccharide is either an aldose (the carbonyl group is at

The simplest aldose, glyceraldehyde, contains one chiral center

What about dihydroxyacetone? Does it contain chiral center?

To represent three-dimensional sugar structures on paper, we

• The hexoses, which include the aldohexose D-glucose and the

Sucrose is common table sugar. It

• The aldopentoses D-ribose and 2-deoxy-D-ribose are

Pyranose (six-membered ring) and furanose (five-membered ring)

Further away from us

Two sugars that differ only in the configuration around one

• sugar derivatives: a hydroxyl group in the parent compound is

• The amino group can be condensed with acetic acid, as in N-

Oxidation of the carbonyl (aldehyde) carbon of glucose to the

Monosaccharides can be oxidized by relatively mild oxidizing

Table sugar: Made by

• A hydroxyl group of one monosaccharide can add to the

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