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Carbohydrates

Teknologi Pangan
Fakultas Teknologi Industri Pertanian
Universitas Sahid Jakarta
Topics of Discussion

 Carbohydrate classification
 Carbohydrate chemistry (structure
and stereoisomer)
References
 Modern Carbohydrate Chemistry (Roger W.
Binkey), Marcel Dekker,Inc
 Carbohydrates in Food (Ann-Charlotte Eliason),
Marcel Dekker,Inc
 Foods Experimental Perspectives (Margaret
McWilliams), Prentice Hall
 Others:
http://www.chem.qmul.ac.uk/iupac/2carb/
(Nomenclature of Carbohydrates)
 Food Theory and Applications (Jane Bowers),
MacMillan Publ. Co.
The Role of Carbohydrate
 One of the most classes of chemical
compounds
 The molecules in which energy from the sun
is stored by photosynthesis.
 An essential structural component of living
cells; includes simple sugars with small
molecules as well as macromolecular
substances.
The Role of Carbohydrate

CO2 + H2O CARBOHYDRATES + O2 + Energy


The Role of Carbohydrate
 Play a major role in human diets
comprising 40-75% of energy intake.
Energy value : 4 kcal/g
 The basis for the manufacture of
sugar, starch, paper, wood pulp,
pharmaceuticals, special chemicals
Definition
 Organic compounds that consist of carbon,
hydrogen and oxygen
 The polyhydroxy aldehydes, ketones,
alcohols, acids, their derivatives, and the
polymers derived from these compounds.
 They vary from simple sugars containing
from three to seven carbon atoms to very
complex polymers.
Classification
Carbohydrates may be classified
according to their degree of polymeri-
zation (DP) and may be divided initially
into three principal groups, namely
sugars, oligosacharides and poly-
saccharides
Classes of carbohydrates
based on functional groups
Name Functional group Example
Glycose Aldehyde/ketone Any monosaccharide
Aldose Aldehyde D-glucose
Ketose Ketone D-fructose
Glycitol or alditol Alcohol D-glucitol
Glyconic or aldonic acid Carboxylic acid D-gluconic acid
Glycaric or aldaric acid Dicarboxylic acid D-glycaric acid
Uronic acid Carboxylic acid, D-glucuronic acid
aldehyde
The major dietary carbohydrates

Class (DP) Sub-Group Components


Sugars (1-2) Glucose, galactose,
Monosacharides
fructose
Disacharides Sucrose, lactose
Polyols Sorbitol, mannitol
Oligosaccharides Malto-oligosacharides Maltodextrins
(3-9) Other Raffinose, stachyose,
oligosaccharides fructo-oligosaccharides
Polysaccharides Amylose, amylopectin,
Starch
(>9) modified starch
Non-starch Cellulose, hemicellulose,
polysaccharides pectins, hydrocolloids
Monosaccharides
 Parent monosaccharides are poly-hydroxy
aldehydes H-[CHOH]n-CHO or polyhydroxy
ketones H-[CHOH]n-CO-[CHOH]m-H with
three or more carbon atoms
 The generic term of ‘monosaccharide’
denoted to a single unit, without glycosidic
connection to other such units
 Cannot be converted hydrolytically into
smaller molecules
Aldoses and Ketoses
 Aldoses: monosaccharides with an
aldehydic carbonyl (-CHO) at C1. Example:
Glyceraldehyde, erythose, ribose, glucose
 Ketoses: monosaccharides with ketonic
carbonyl (-C=O) at C2. Example: fructose,
sorbose
Reducing sugar
 Sugar with aldehydic carbonyl group has a
reducing power
 Reducing property is determined by the
presence of free OH in C1
 Example: glucose, lactose
Structural Representation

 Fischer projection formula (acyclic


systems)
 Haworth projection formula (cyclic
systems: pyranoid, furanoid)
Structural Representation
(Fischer Projection)
ALDOSES KETOSES
Stereoisomer
 The orientation of other groups attached to the
carbon chain of carbohydrates affects the properties
and interactions of monosaccharide.
 The alternative forms of a molecule in which atoms
or groups attached to the carbon chain point in
different direction are termed stereoisomer.
 Stereoisomer are identified as D- or L- depending on
the directions pointed by atoms attached to the
carbon chain.
 In most cases, the D-form of the monosaccharide, is
much more common than L- forms among cellular
carbohydrates.
Stereoisomer
 Many C atoms of monosaccharide are
asymmetric  each of their four covalent
bonds links to a different atom or chemical
group.
 For example: the middle C of glyceraldehyde
is asymmetric because it shares electrons in
covalent bonds with -H, -OH, -CHO, and
-CH2OH.
Stereoisomer
 The groups attached to asymmetric carbon atoms
can take up either of two fixed position with
respect to other C atoms in a chain. In
glyceraldehydes the -OH group can extend either
to the left or to the right of the C chain with
reference to the -CHO and -CH2OH groups.
 The -OH extends to the right is called D-
glyceraldehydes (from the Latin dexter= right)
 The -OH extends to the left is L-glyceraldehyde
(from laevus = left).
CHO CHO CHO CHO CHO CHO

HCOH HOCH HCOH HOCH HCOH HOCH

HCOH HCOH HOCH HOCH HCOH HOCH

HCOH HOCH HCOH HCOH HOCH HOCH

HCOH HOCH HCOH HCOH HCOH HCOH

CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH

D-Allose L-Glucose D-Glucose D-Mannose D-Gulose D-Talose

ALDOSES
CHO CHO CHO CHO CHO CHO

HOCH HCOH HCOH HOCH HCOH HOCH

HCOH HOCH HCOH HCOH HOCH HOCH

HOCH HOCH HCOH HCOH HCOH HCOH

HCOH HCOH CH2OH CH2OH CH2OH CH2OH

CH2OH CH2OH

D-Idose D-Galactose D-Ribose D-Arabinose D-Xylose D-Lyxose

ALDOSES
CH2OH CH2OH CH2OH CH2OH

O=C C=O C=O C=O

HCOH HOCH HCOH HCOH

HOCH HCOH HOCH HCOH

HOCH HCOH HCOH CH2OH

CH2OH CH2OH CH2OH

L-Fructose D-Fructose D-Sorbose D-Pentulose

KETOSES
=
H OH = HO H
C CHO C

HCOH HCOH HCOH

HOCH O HOCH HOCH O


HCOH HCOH HCOH

HC HCOH HC

CH2OH CH2OH CH2OH

-D-Glucose D-Glucose -D-Glucose

The structure is not linear  Oxygen bridge


between C1 and C5
Structural Representation
(Haworth Projection)
 In the six-carbon monosaccharide
(glucose), a covalent bond can form
through a reaction between the aldehyde at
C1 and the -OH at C5  produces
glucopyranose ring structures.
 The ketone at C2 (in fructose) can also
react with the OH at C5  produce a gluco-
furanose ring
Pyranose and Furanose
6
H2COH 6 O 1 CH2OH
HOCH2
5 O
H H
H 5 2
4 OH 1 H
H HO OH
H
OH OH
3 2 4 3
H OH OH H

-D-glucopyranose -D-glucofuranose
( -D-glucose) ( -D-fructose)
CHO CH2OH
HCH2OH
HCOH C=O HOCH2 O CH2OH
HO O H
HOCH H HOCH
OH H H HO
HOCH HCOH H OH
H OH
HCOH HCOH
H OH OH H
CH2OH CH2OH

D-Galactose D-Fructose
Nomenclature
6
HCH2OH =D
 In -D-glucopyranose, the H
5 O H
“pyranose” portion of the H
4 1
name refers to the pyranoid OH H

ring in the molecule OH


2
OH
3
 The D designator specifies H OH
the configuration at C5 (the
-D-glucopyranose
chiral center farthest from
( -D-glucose)
the reference group)
Nomenclature
6
HCH2OH

 Stereochemistry at C1 is H
5 O H
H
given by  4 1
OH H
 Prefix: “gluco” OH OH
3 2
 If the configuration at H OH
=

C1 is inverted, -D-
-D-glucopyranose
glucopyranose is formed ( -D-glucose)
Nomenclature
6 O 1 CH2OH
 A five-membered ring: HOCH2

furanose 5 2
H HO
 The D designator H OH

specifies the 4 3

configuration at C5 (the OH H

chiral center farthest -D-fructofuranose


from the reference ( -D-fructose)
group)
Nomenclature
6 O 1 CH2OH
HOCH2
 Stereochemistry at C2 is
5 2
given by  H HO OH
H
 Prefix: “fructo” =
4 3
 If the configuration at OH H
C1 is inverted, -D-
-D-fructofuranose
glucofuranose is formed ( -D-fructose)
Structural Representation
(Haworth Projection)
The glucospyranose ring occurs in two forms
that differ only in the orientation of the -OH
group at C1:

• -OH group points downward, in the alpha


() form of the sugar, as in -glucose.
• -OH group points upward from the ring in
a beta () position of the sugar as in -
glucose.
Structural Representation
(Haworth Projection)

 Starches, which are assembled from


-glucose units, are soluble and
easily digested.
 Cellulose, synthesized from -glucose
units, is insoluble and cannot be
digested as a food source by most
animals.
Disaccharides
 Monosaccharides in the ring form can link
together to form disaccharides or in greater
numbers to form polysaccharides.
 Disaccharides are formed when two
monosaccharides are coupled together.
 The coupling is of a specific type: an oxygen
atom forms a bridge between the units coupled
together
 This oxygen atom must be part of an acetal or
ketal group.
Disaccharides
 Linkage of two monosaccharide molecules
to form the disaccharides such as maltose,
lactose and sucrose. The linkages are
designated as alpha () or beta ()
depending on the orientation of the -OH
group at the number C1 forming the bond.
 The linkage are called glycosidic linkages
and are know as alpha () or beta () 1-2,
1-3, 1-4, and1-6.
Disaccharides
Oligosaccharides
 Formed when small numbers of
monosaccharides are coupled together.
 Example: raffinose, stachyose, fructo-
oligosaccharides, maltodextrin
Polysaccharides

 Starch (amylose & amylopectin)


 Cellulose
 Hemicellulose
 pectins, hydrocolloids
Starch
 Starch consists of two types of molecules, amylose
(normally 20-30%) and amylopectin (normally 70-80%).
Both consist of polymers of a-D-glucose units in the
conformation (D-glucopyranose molecules).
 In amylose these are linked -(14)-, with the ring
oxygen atoms all on the same side, whereas in
amylopectin about one residue in every twenty or so is
also linked -(16)- forming branch-points.
 The relative proportions of amylose to amylopectin and -
(16)- branch-points both depend on the source of the
starch, e.g. amylomaizes contain over 50% amylose
whereas 'waxy' maize has almost none (~3%)
Amylopectin
A naturally occurring branched
polymer of glucose found in
starch whose linear portions are
connected by -1,4-glycosidic
linkages and the branch points
are -1,6-glycosidic linkages
Amylose
A naturally occurring polymer of
glucose found in starch comprised
of anhydroglucose units with -
1,4-glycosidic linkages in straight
chain
The polymerization of glucose into amylose
The difference between amylose and cellulose
Polysacharides

Amylopectin
Structure of Amylopectin