Biochemistry

MACROMOLECULES A. STRUCTURE AND NOMENCLATURE

• Monosaccharides (General Formula:

C n H 2 n On)

• Most common monosaccharides have 3 – 9

carbon atoms.

• ~ose suffix. Prefixes, indicate the number of

carbon atoms. (ex. Aldotriose and ketotriose)

• Aldoses – monosaccharide with aldehyde

group.

• Ketoses – monosaccharide containing ketone

group.

CARBOHYDRATES

 Are the most abundant organic compounds in

the plant world.

 Act as store houses of chemical energy.

(glucose, starch glycogen)

 Components of supportive structures. B. FISCHER PROJECTION FORMULAS

(Cellulose) • Show the configuration of carbohydrates.
 Connective tissues in animals; and • Two dimensional representations showing the
 Essential components of nucleic acids. configuration of a stereocenter; horizontal
and vertical lines represents bonds
CARBOHYDRATES: “HYDRATE OF CARBON”

• Polyhydroxylaldehydes or
polyhydroxylketones or substances that give
these compounds on hydrolysis.

• Latin: “saccharum” = sugar

• Classification of Carbohydrates:

• Monosaccharides

• Disaccharides

• Oligosaccharides or Polysaccharides
(depends on no. of simple sugars)
 • The first two are aldohexose and the third is
ketohexose.

• Glucose is the most abundant aka dextrose

bec it is dextrorotatory

C. D – AND L – MONOSACCHARIDES

• D – Monosaccharide  When written as a

Fischer projection, has the –OH group on its
penultimate carbon to the right.

• L – Monosaccharides  When written as a

Fischer projection, has the –OH group on its CONFIGURATIONAL RELATIONSHIP OF KETOSES
penultimate carbon to the left.

• Penultimate carbon  Second to the Last

carbon.

CONFIGURATIONAL RELATIONSHIP OF ALDOSES

• Each name consist of 3 parts:

• D – specifies the configuration at the

stereocenter farthest from the carbonyl
group.

• Prefixes

• Suffix –ose indicates that a compound is DRAWING FISCHER PROJECTIONS: (MIRROR IMAGE)
carbohydrate.
• D-Erythrose
• The most common hexoses in the biological
world are D-glucose, D-galactose, and D- • D – Threose
fructose.
 D. AMINO SUGARS

• Monosaccharides in which an –OH group is

replaced with an –NH2 group.

• Glucosamine – components of many A. HAWORTH PROJECTIONS

polysaccharides, including connective tissue • A way to view furanose and pyranose forms of
such as cartilage. monosaccharides.
• Chitin – found in exoskeleton animals. • Anomeric carbon – hemiacetal carbon of the
• Components of naturally occurring antibiotics. cyclic form of a monosaccharide.

• Anomers – Monosaccharides that differ in

configuration only at their anomeric carbons

• Furanose – a five membered cyclic hemiacetal

form of monosaccharide.

• Pyranose – A six membered cyclic hemiacetal

form of a monosaccharide.

GALACTOSEMIA

Happens when a person cannot utilize the monosaccharide galactose.

Galactose is part of lactose (Milk sugar)

Effect: (Infants)

Mental retardation

Failure to grow

DRAWING HAWORTH PROJECTIONS

Cataract formation

Severe cases can lead to death

E. PHYSICAL PROPERTIES OF MONOSACCHARIDES

• Colorless and crystalline solid.

• Soluble in water because of hydrogen

bonding.

• Slightly soluble in ethanol and are insoluble in

non polar solvents.

CYCLIC STRUCTURES OF MONOSACCHARIDES

• hemiacetal is an alcohol and ether ATTACHED

TO THE SAME CARBON
 Glycoside – carbohydrate in which the –OH group on
its anomeric carbon is replaced with an –OR group

Glycosidic bond – The bond from the anomeric

carbon of a glycoside to an – OR

We name glycosides by listing the alkyl or aryl group

bonded to oxygen followed by the name of the
carbohydrate which ending –e is replaced by –ide.

GLYCOSIDIC BOND

B. CONFORMATION AND REPRESENTATION

• Chair conformation – a representation of a GLYCOSIDE

six-membered ring.

B. REDUCTION TO ALDITOLS

• Alditols – Products formed when the CHO

L – ASCORBIC ACID (VITAMIN C) group of a monosaccharide is reduced to a
CH 2 OH group.
• Structure resembles that of a
monosaccharide.

• Synthesized both biochemically by plants and

some animals and commercially from glucose.

• Necessary tom maintain the structure of

collagen in the skin and in the blood vessels.

C. MUTAROTATION C. OXIDATION TO ALDONIC ACIDS (REDUCING

SUGARS)
• The change in specific rotation that occurs
when alpha or beta form of a carbohydrate is • Reducing sugar – A carbohydrate that reacts
converted to an equilibrium mixture of the with a mild oxidizing agent under basic
two forms. conditions to give an aldonic acid.

CHARACTERISTIC REACTIONS OF
MONOSACCHARIDES

A. Formation of glycosides (Acetals)

 • Important intermediates in the metabolism of
monosaccharides.

• This is the first step in glycolysis.

D. OXIDATION TO URONIC ACIDS

• In humans it serves as an important DISACCHARIDES AND OLIGOSACCHARIDES

component of the acidic polysaccharides of
connective tissues.
Disaccharides – Carbohydrates containing two
• Detoxify foreign phenols and alcohols. monosaccharides unit joined by a glycosidic
bond.
• In the liver these compounds are converted as
glycosides of glucuronic acid (glucoronides)
and excreted in the urine Oligosaccharide – A carbohydrate containing
from six to ten monosaccharides units, joined
by glycosidic bond.

Polysaccharides – Carbohydrate containing a

large number of monosaccharide units, each
joined to the next by one or more glycosidic
bond

A. SUCROSE

• Table sugar

• The most abundant disaccharide in the

biological world.

• It is obtained principally from the juice of

sugar cane or sugar beats.

E. THE FORMATION OF PHOSPHORIC ESTERS

 B. LACTOSE

• Principal sugar present in milk.

• 5 to 8% human milk; 4-6% of cow’s milk

POLYSACCHARIDES
• A reducing sugar. (Aldehyde group is exposed
• Consist of large number of monosaccharide
and can be oxidized)
units bonded by glycosidic bond.

• Three important polysaccharides: all made up

of glucose unit.

• Starch: Amylose and Amylopectin

• Glycogen

• Cellulose Consist of large number of

monosaccharide units bonded by glycosidic
bond.

• Three important polysaccharides: all made up

C. MALTOSE of glucose unit.
• Derives it’s name from the presence of malt, • Starch: Amylose and Amylopectin
the juice from sprouted barley and other
cereal grains. • Glycogen

• A reducing sugar • Cellulose

A. STARCH: AMYLOSE AND AMYLOPECTIN

• Energy storage for plants.

• Can be separated in two principal

polysaccharide: Amylose and amylopectin.

• Complete hydrolysis of both amylose and

amylopectin yields only to D-Glucose.

• Amylose: 4000 glucose ; Amylopectin: 10,000

D-Glucose

B. GLYCOGEN

• Act as the energy reserve carbohydrate for

animals.
D. RELATIVE SWEETNESS
• The total amount of glycogen in the body of a
well nourished human adult is about 350g
divided almost equally between liver and
muscle cells.
 C. CELLULOSE

• The most widely distributed plant skeletal

polysaccharide, constitutes almost half of the
cell-wall material of wood.

• Cotton is almost pure cellulose.

• Humans and other animals cannot use

cellulose as food, because our digestive
systems do not contain Beta-Glucosidases,
enzymes that catalyze the hydrolysis of Beta-
glucosidic bonds.

ACIDIC POLYSACCHARIDES

• Contains carboxyl group and/or sulfuric ester

groups.

• Plays an important role in connective tissues,

because they contain amino sugars.

• Glycosaminoglycans – acidic polysaccharides

that interact with collagen to form tight or
loose networks.

A. HYALURONIC ACID

• The simplest acidic polysaccharide present in

connective tissue.

• It is most abundant in embryonic tissues and

in specialized connective tissues such as
synovial fluid, the lubricants of joints in the
body, and vitreous in the eye.

• Common ingredient of lotions, moisturizers

and cosmetics.

B. HEPARIN

• A heterogeneous mixture of variably

sulfonated polysaccharide chains.

• Synthesized and stored in the mast cells (cells

that are part of the immune system and that
occur in several types of tissues)

IS THERE A CONNECTION BETWEEN

CARBOHYDRATES AND OBESITY?