7

CARBOHYDRATE
S

Summary taken from the books: BIOCHEMISTRY by

Lehninger, 4th Ed., J.T. Moore and BIOCHEMISTRY by L.
Stryer and Enzyme Kinetis by Carruters, D.
October, 2013
Summarized by Eugenia Olivera
CARBOHYDRATES

 Animals for the

most part obtain
carbohydrates
from plants, where
they are a means
of storing energy

 In plants
carbohydrates
have other roles in
addition to energy
storage
http://abhsscience.wikispaces.com/B-Block+Photosynthesis
 CARBOHYDRATES
The nature of the covalent bonds linking the
monosaccharides in a polysaccharide are much
more varied than the canonical peptide bond of
proteins.

The variety of monosaccharides and the

multiplicity of linkages forming polysaccharides
mean that carbohydrates provide cells with a
vast array of three-dimensional structures that
can be used for a variety of purposes, as simple
as energy storage or as complex as cell–cell
recognition signals.
CARBOHYDRATES
General Functions:

1) Source of energy
2) Energy reserve
The oxidation of carbohydrates is the central
energy-yielding pathway in most non
photosynthetic cells.
3) Structural roll
Insoluble carbohydrate polymers serve as
structural and protective elements in the cell
walls of bacteria and plants and in the
connective tissues of animals.
4) More complex functions
Glycoproteins: in cell membranes linked to
proteins
Lectins: information-rich molecules that guide
many biological processes.
Carbohydrates are compounds containing C, H and O

With a general formula Cx(H2O)y

They are polyhydroxy aldehydes or ketones, or

substances that yield such compounds on hydrolysis.

(CH2O)n; some also contain nitrogen, phosphorus, or

sulfur.

All have C=O and –OH functional groups.

Classified based on:

-Size of base carbon chain

-Number of sugar units
-Location of C=O
-Stereochemistry
 Classification based on number of sugar
units
Aldoses
Monosaccharid
e
Ketoses

Sugars Di

Carbohydrates
Polysaccharide
Tri
s
Oligosaccharid
es
Tetra

Etc.
 Classification based on location of C=O

Aldehyc product of a Ketonic product of a

polyvalent alcohol. polyvalent alcohol.
Aldose-aldehyde C=O Ketose-ketone C=O
Representative
monosaccharides:

(a) Two trioses, an aldose and a

ketose.

(b) Two common hexoses.

(c) The pentose components of

nucleic acids.
D-Ribose is a component of
ribonucleic acid (RNA), and 2-deoxy-
Dribose
is a component of deoxyribonucleic
acid (DNA).
ALDOSES

Most Part of milk

important in sugar
diet
 KETOSES
Sweetest of
all sugars

Aldoses and ketoses.

The series of (a) D-aldoses and
(b) D-ketoses having from three
to six carbon atoms, shown as
projection formulas.
The carbon atoms in red are chiral
centers.
In all these D isomers, the chiral
carbon most distant from the
carbonyl carbon has the same
configuration as the chiral carbon in
D-glyceraldehyde.
The sugars named in boxes are the
most common in nature.
Carbohydrates can exist in a dazzling variety of
isomeric forms.

Dihydroxyacetone and glyceraldehyde are

called constitutional isomers because they
have identical molecular formulas but differ in
how the atoms are ordered.

Stereoisomers are isomers that differ in spatial

arrangement.
Glyceraldehyde has a single asymmetric
carbon atom and, thus, there are two
stereoisomers of this sugar: D-glyceraldehyde
and L-glyceraldehyde.

These molecules are a type of stereoisomer

called enantiomers, which are mirror images of
Stereoisomers

Stereochemistry: study of spatial arrangement of

molecules.

Stereoisomers: are mirror images of each other

and they have…
• the same order and types of bonds.
• different spatial arrangements.
• different properties.

Many biologically important chemicals, like

sugars, exist as stereoisomers.
Your body can tell the difference.
Three ways to represent the two
stereoisomers of glyceraldehyde:

The stereoisomers are mirror images

of each other.

Balland-stick models show the actual

configuration of molecules.

By convention, 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.

Recall that in perspective formulas,

solid wedge-shaped bonds point
toward the reader, dashed wedges
point away.
SUGARS DO NOT REGULARLY
EXISTS AS “LINEAR” MOLECULES
 They form cyclic or circularized
molecules
 Aldehydes form pyranoses
KETOSES FORM
FURANOSES
 Note 5 atom ring versus 6 atom ring
HAWORTH PROJECTIONS-
ALPHA AND BETA ANOMERS

Carbons are numbered from the carbonyl end of the sugar

HAWORTH AND OTHER
REPRESENTATIONS
MONOSACCHARIDES CAN
BE MODIFIED
 Describe a
modified
monosaccharide
relevant for your
area of expertise
MONOSACCHARIDES CAN BE LINKED
TO FORM COMPLEX CARBOHYDRATES
Because sugars contain many hydroxyl groups, glycosidic bonds
can join one monosaccharide to another.
Oligosaccharides are built by the linkage of two or more
monosaccharides by O-glycosidic bonds.
In the disaccharide maltose, for example, two D-glucose residues
are joined by a glycosidic linkage between the anomeric form of C-
1 on one sugar and the hydroxyl oxygen atom on C-4 of the
adjacent sugar. Such a linkage is called an -1,4-glycosidic bond.
 Activated (energy rich) sugar nucleotide,
such as UDP-glucose (UDP is the
abbreviation for uridine diphosphate)

Oligosaccharides are
synthesized through
the action of specific
enzymes,
glycosyltransferases,
which catalyze the
formation of glycosidic
bonds.

Given the diversity of

known glycosidic
linkages, many
different enzymes are
required.
 - Describe each
disaccharide
Sucrose - Identify the enzymes
that hydrolyze the
Lactose glyosidic bond on
each
Maltose - Locate the tissue
where they work
- Identify the main role
in human metabolism
Sucrose
Lactose
Maltose
Lactose, the disaccharide of milk, consists of
galactose joined to glucose by a -1,4-glycosidic
linkage.
Lactose is hydrolyzed to these monosaccharides
by lactase in human beings and by b-
galactosidase in bacteria.
In maltose, two glucose units are joined by an -
1,4-glycosidic linkage. Maltose comes from the
hydrolysis of large polymeric oligosaccharides
such as starch and glycogen and is in turn
hydrolyzed to glucose by maltase.
Sucrase, lactase, and maltase are located on the
outer surfaces of epithelial cells lining the small
intestine. The cleavage products of sucrose,
lactose, and maltose can be further processed to
provide energy in the form of ATP.
VAST MAJORITY OF CARBOHYDRATES
ARE IN POLYMERIC FORMS
 Wood is made up of:
 35% lignin
 65% carbohydrate

 Of the carbohydrate portion the majority is

cellulose with is a polymer of 1,4,b-glucose
LIGNIN
 Lignin binds together cellulose fibers
into bundles and links bundles, giving
the fiber strength
 GLYCOGEN
 Glycogen, a glucose polymer constructed from α-1,4 and α-
1,6 linkages, is a major storage form of carbohydrates in
most organisms. In animals (including humans), large
reservoirs of glycogen can be found in the liver and muscle.
As a food component, glycogen is contained in shellfish such
as oysters and mussels, and it has been thought to bestow
health benefits for a long time.
STARCH
 Another major polymer of glucose
 Utilizes a different linkage
CELLULOSE AND STARCH
 Cellulose forms a linear non-branching
molecule

 Because of the bond angle between

monomers starch forms a spiral strand
that is capable of branching
CELLULOSE AND STARCH
 Cellulose is
beta-glucose
monomer
 Starch is an
alpha-glucose
monomer
 Basically the
position of the
alcohol group
at position C1

Human enzymes digest starch with alpha-amylase and cannot

digest cellulose
ENZYMES CAN REDUCE EITHER
POLYMER DOWN TO MONOMER
SUGARS
 Cells do not use these polymers as a
source of energy but must first
enzymatically digest the polymer.

 Polymers that cannot be digested, they

form the heterogeneous class of
“dietary fiber”.
Define Dietary
Fiber
FIBER FROM FRUITS
 Efectos fisiológicos de la fibra
dietaria antioxidante
Fibra
Fracción Fracción
soluble insoluble

Aumenta la sensación de saciedad

Formación de geles Hinchamiento
viscosos
Aumento de volumen

Retarda el vaciamiento
gástrico
Hace más eficienteEstimulación de paredes
la intestinales
Aumenta la distención
gástrica
digestión
Eliminación de compuestos
nocivos

* Liaron, 1997; López, 1997, Brown, 1996; Tiwary, 1997 38

 Mecanismo de acción
hipoglucemiante de la fibra dietaria
antioxidante

FS + FI
(1 - 6) glucosidasa
Matriz del alimento
(isomaltasa) a(1-4) amilasa

Glucosa
Glucosa
Glucosa
Glucosa
Glucosa
Glucosa

Absorbidas en
lumen intestinal  GLUCOSA
GLUCOSA
POSTPRANDIAL
 Efectos fisiológicos de la fibra
dietaria antioxidante en el colon

ambiente
fibra antioxidante
Fracción
FS + FI
soluble
Matriz del alimento
FEW CAN IMAGINE A WORLD
WITHOUT CELLULOSE AND
STARCHES
 Wood
 Paper—cardboard, paper, toilet paper
 Flour—bread, cookies, crackers
 Adhesives—glues, binders
 Fabrics—cotton, flax, hemp
 Thickening agents—sauces
 Rigidity agents—fabrics and papers
 Moisture absorption—anti-caking agents
WHAT GIVE THESE POLYMERS
DIFFERENT CHARACTERISTICS?
 Polymer length
 Lignin
 Branching
 Component sugars
DIFFERENT CELLULOSES
AND STARCHES
 Quality of paper is largely determined by
cellulose fiber length, the longer the fiber
the more durable the paper
 Money
 Toilet paper

 Starch granules and branching

 Granules respond differently to wetting,
mechanical agitation, and heat
 Different branching patterns give different
mechano-physical properties
 Cake flour, pasta flour, and cracker flour differ in
degree of branching
 CARBOHYDRATES LINKED
TO PROTEINS
 Sugars are linked to extracellular
proteins where they stabilize the protein

Many glycoproteins are

components of cell
membranes, where they play
a variety of roles.
The carbohydrate parts of
membrane glycoproteins are
on the outer surface of the
cell membrane.
Many secretory proteins are
glycoproteins.
 Describe a
glycoprotein that
you find
interesting
LECTINS ARE PROTEINS THAT
BIND TO SPECIFIC SUGARS
 Concanavalin A—α-D-mannosyl and α-D-
glucosyl
 Peanut agglutinin--galactosyl (β-1,3) N-
acetylgalactosamine
 Used to stimulate cells and as
purification tool for glycosylated
proteins