CARBOHYDRATES - may be classified according to the number of  Hemiacetal = monosaccharide +

- most abundant organic compound in the carbons contained or according to the alcohol
world functional group present  Acetal = hemiacetal + alcohol
• includes not only sugar but also starch CLASSIFICATION ACCORDING TO NUMBER OF FISCHER PROJECTION FORMULA (LINEAR)  Pyranose and Furanose
(bread, pasta, rice) CARBONS - are used because
• act as store houses of chemical energy # of Carbons Class of Monosaccharide monosaccharide 5- and 6-
• components of supportive structures in 3 Triose membering rings correspond
plants 4 Tetrose - the ring is drawn flat and viewed
• connective tissues in animals 5 Pentose through its edge with the
• essential components of nucleic acids 6 Hexose anomeric carbon (new C [Chiral]
• means “hydrate of carbon” 7 Heptose stereocenter created in forming
• derives from the formula Cn(H2O)n 8 Octose the cycling structure)
 Glucose: C6H12O6 or C6(H2O)6 9 Nonose
• most are polyhydroxyaldehydes,  β means that the -OH on the
polyhydroxyketones, or compounds that yield CLASSIFICATION ACCORDING TO  D- and L- Monosaccharides anomeric carbon lies on the same
them after FUNCTIONAL GROUP - D-Monosaccharide – has the -OH side of the as the terminal -CH2OH
hydrolysis ALDOSES group penultimate carbon to the  α means that the -OH on the
- monosaccharides containing aldehyde group right anomeric carbon lies on the side of
Polyhydroxyaldehyde O
Many OH ||
- L-Monosaccharide – has the -OH the ring opposite from the terminal
H O
C-H group on its penultimate to the CH2OH
\ //
C left
Polyhydroxyketone O |
Many OH || R Penultimate second
C-C-C L – Levorotatory
to the last carbon
KETOSES D – Dextrorotatory
- ose indicates that a molecule is a - monosaccharides containing ketone group
carbohydrate O HAWORTH PROJECTION FORMULA (CYCLIC) α β
- Saccharides – simpler members of the CHO ||
C
family (Latin: saccharum-sugar) [pero SUGAR DERIVATIVES
/ \
sacchararum sa google] R R’  Deoxy Sugar (deoxyribose)
- Monosaccharide, Disaccharide, 1 OH  H
Oligosaccharide and Polysaccharide MOST ABUNDANT HEXOSES  Amino Sugar (glucosamine)
 D-Glucose 1 OH  NH2
A. MONOSACCHARIDE  D-Galactose  Alcohol Sugar/Alditol (xylitol)
- ex. glucose o D-Aldohexoses C=O (carbonyl group)  OH
- C6H12O6  D-Fructose  -pyran- a 6-membered hemiacetal  Carboxylic Acid Sugar/Aldonic Acid
- simplest of CHO since they contain only one o D-Ketohexose ring (gluconic acid)
polyhydroxyaldehyde or ketone unit  -furan- a 5-membered hemiacetal C=O  COOH
- have 3 to 9 carbon atoms ring
Amino Sugars
 D-Glucosamine
 D-Mannosamine
 D-Galactosamine
REACTION OF MONOSACCHARIDES
1.Reduction to Produce Sugar
Alcohols/Alditol
- carbonyl group is reduced to hydroxyl group
using hydrogen as the reducing agent (sugar
alcohol)
- drop -ose and change to -itol
2.Formation of Glycosides (Acetals)
• Acetal – yields when hemiacetal (derived
from aldehyde) is treated with one molecule
of alcohol
• Glycoside – a carbohydrate in which the -OH
group on its anomeric carbon is replaced by
an -OR group
• Glycosidic Bond – the bond forms the
anomeric carbon of a glycoside to an -OR
group
3.Phosphate Esters Formation
• important in the metabolism of
monosaccharides
• e.g. conversion of glucose -6- phosphate
4.Oxidation to Uronic Acids
• enzyme catalyzed oxidation of the primary
alcohol at carbon 6 of a hexose yields a uronic
acid
5.Oxidation to Produce Acids Sugars/Aldonic
Acid
• aldehyde group of an aldose can be oxidized
under basic conditions to a carboxylate group
PHYSICAL PROPERTIES
- colorless, crystallize solids
• are very soluble in water
- Because hydrogen bonding is
possible between there polar
-OH group and water
• slight soluble in ethanol
- Insoluble in nonpolar solvent
such as diethyl ethel,
dichloromethane, and benzene
• sweet and solid in temperature
B. DISACCHARIDES AND OLIGOSACCHARIDES
• Disaccharide
- Contain 2 monosaccharide units
joined by a glycosidic bond
[Dehydration in synthesis; release H2O;
Hydrolysis]
• Oligosaccharide
- to describe any of carbohydrates
that contain from 6 to 10
monosaccharide units
• Polysaccharide
- a carbohydrate containing a
large number of monosaccharide
units, each joined to the next by
one or more glycosidic bonds
Disaccharides
• Lactose – principal sugar present in milk
- consist of D-galactopyranose and
D-glucopyranose
- reducing sugar
- B-1,4 -glycosidic bond
• Maltose – derives its name from its
presence in malt, the juice from sprouted
berley and other cereal grains
- Consist of 2 units of D-
glucopyranose
- Reducing sugar
- α – 1,4 – glycosidic bond
• Sucrose (table sugar) – most abundant
disaccharide
- obtained principally from the
juice of sugar cane and sugar
beets
- nonreducing sugar
- α, β - 1,2 - glycosidic bond
Relative Sweetness
• Fructose – sweetest even sweeter than
sucrose
- Honey – D-fructose and D-
glucose
• Lactose – almost no sweetness and is
sometimes added to food as a filler
C. POLYSACCHARIDES
General Characteristics
• contains very long chains of hundreds or
thousands of monosaccharide units, which
may be either in straight or branched chains
• Homoglycan/Heteroglycan
Starch: Amylose and Amylopectin
- For energy storage in plants
- Complete hydrolysis yields only
D-Glucose
Amylose – composed of continuous,
unbranched chains of as many as 4000 D-
glucose units joined by α-1,4-glycosidic bonds
Amylopectin – highly branched; contains
chains of as many as 10,000 D-glucose units
joined by α-1,6-glycosidic bonds and α-1,4-
glycosidic bonds
• Glycogen – acts as the energy-reserve
carbohydrates for animals
- It is branched polysaccharide
containing approximately 106
glucose units joined by α-1,4 and
α-1,6-glycosidic bonds
Glycogenesis (excess): glucose  glycogen
Glycogenolysis (fasting): glycogen  glucose
• Cellulose – most widely distributed plant
skeletal polysaccharide [most abundant
carbohydrate in the whole world]
- Is a linear polysaccharide of D-
glucose units joined by β-7,4-
glycosidic bonds
- Unbranched
• Chitin – second most abundant
- Gives rigidly to the exoskeleton
of crabs, lobster, shrimp, insects
and other arthropods
- Found in the cell walls of fungi
- Monosaccharide: N-acetyl-D-
Glucosamine (NAG)
- Contain both glycosidic linkage
and amine bonds, can be broken
by hydrolysis (D-Glucosamine)
• Hyaluronic Acid – contains alternating
residues of N-acetyl-β-D-Glucosamine and D-
Glucoronate
- Product when the -CH2OH group
of glucose is oxidized to a -COOH
group
• Heparin – highly sulfated polysaccharide
with only 15-90 disaccharide residues per
chain
- Monosaccharides
Sulfate derivative of D-glucuronate (D-
glucuronate-2-sulfate)
Doubly sulfated derivative of D-Glucosamine
(N-sulfo-D-Glucosamine-6-Sulfate)