Biokim 3 - Bu Asih - KARBOHIDRAT

Carbohydrate
Kuliah Biokima Dasar Minggu III

3/29/2020 Lab. Biokimia Nutrisi 1
CARBOHYDRATE
 Carbohydrates are the most abundant biomolecules
on Earth
 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
 Are Composed Of Carbon, Hydrogen, And Oxygen
In The Ratio Of Two Hydrogens And One Oxygen
For Each Carbon
There are three major size classes
of carbohydrates:
1.Monosaccharides
2.Oligosaccharides
3.Polysaccharides
(the word “saccharide” is derived

from the Greek sakcharon,
meaning “sugar”).

I.MONOSACCHARIDES
TRIOSE C3H6O3 GLYCERALDEHYDE
PENTOSE C5H10O5 RIBOSE
HEXOSES C6H12O6 GLUCOSE
II.OLIGOSACCHARIDES ( 2-10 MONOMER)

DISACCHARIDES C12H22O11 MALTOSE, SUCROSE
TRISACCHARIDES C18H32O16 RAFFINOSE (F-GL-GAL)

III. POLISACCHARIDES
PENTOSE (C5H8O4) X XYLAN
POLYMERS (POLYXYLOSE)
HEXOSE (C6H10O5) X STARCH

POLYMERS (POLYGLUCOSE)

Monosaccharides
• simple sugars
• consist of a single
polyhydroxy aldehyde
or ketone unit
• The most abundant
monosaccharide in
nature is the six-carbon
sugar D-glucose,
sometimes referred to
as dextrose.
• Monosaccharides of
more than four carbons
tend to have cyclic
structures. Kuliah Biokima Dasar Minggu III
Properties of monosaccharides
1. STEREOISOMERS: isomers having the same structural
formula but differing in the arrangement of atoms or groups
of atoms in three-dimensional space
All the monosaccharides except dihydroxyacetone contain
one or more asymmetric (chiral) carbon atoms: in optically
active isomeric forms
A carbon atom that has four different groups attached is a
chiral carbon
If a molecule contains one or more chiral carbons, it is likely
to exist as two or more stereoisomers
Kuliah Biokima Dasar

Minggu III Lab. Biokimia
3/29/2020 12 Nutrisi
2. Enantiomers: a type of stereoisomer
Molecules that are (nonidentical) mirror images of
each other are called enantiomer
A key characteristic of enantiomers is that they
have a carbon atom to which four different groups
are attached

 H. Emil Fischer, a German chemist, developed the

convention commonly used for writing two-dimensional
representations of the monosaccharides

 monosaccharide can be divided into two

groups that differ in the configuration about
the chiral center most distant from the
carbonyl carbon.
• When the hydroxyl group on the reference
carbon is on the right the sugar is the D
isomer; when on the left, it is the L isomer.
• Of the 16 possible aldohexoses, eight are D
forms and eight are L.
• Most of the hexoses of living organisms are D
isomers

Isomer

Type & Number of Stereoisomers (optical isomers) :
 Diastereomer
 not mirror images, differ at 2 asymetric center
 Enantiomer
 mirror images
 Epimer
 differ at only one asymetric center

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The Vaht Hoff rule
 Max possible number of optical isomers of

compound = 2n , n is number of asymmetric
centers
 D & L series of sugar
 2 aldotetroses
 4 aldopentoses
 8 aldohexoses
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STUCTURE OF MONOSACCHARIDES
 In aqueous solution, all monosaccharides with five or more
carbon atoms predominantly as cyclic (ring) structures
 carbonyl group has formed a covalent bond with the oxygen of a
hydroxyl group along the chain.
 The formation of these ring structures is the result of a general
reaction between alcohols and aldehydes or ketones to form
derivatives calledhemiacetals or hemiketals
https://saylordotorg.github.io/text_the-basics-of-general-organic-and-biological-chemistry/s04-
chemistry-matter-and-measureme.html
3/29/2020 24 Nutrisi
STUCTURE OF MONOSACCHARIDES
 There is an additional asymmetric carbon atom and thus

can exist in two stereoisomeric forms: and β (example :
-D-glucopyranose and β -D-glucopyranose)

3/29/2020 26 Nutrisi
Oligosaccharides
 consist of short chains of monosaccharide units, or residues,
joined by characteristic linkages called glycosidic bonds.
 The most abundant are the disaccharides, with two
monosaccharide units.
 Typical is sucrose (cane sugar), which consists of the six-
carbon sugars D-glucose and D-fructose.
 All common monosaccharides and disaccharides have names
ending with the suffix “-ose.”
 In cells, most oligosaccharides consisting of three or more units
do not occur as free entities but are joined to nonsugar
molecules (lipids or proteins) in glycoconjugates.

POLYGOSACCHARIDES
are sugar polymers containing more than 20 or so
monosaccharide units, and some have hundreds or thousands
of units.
Some polysaccharides, such as cellulose, are linear chains;
others, such as glycogen, are branched.
Both glycogen and cellulose consist of recurring units of D-
glucose, but they differ in the type of glycosidic linkage and
consequently
have strikingly different properties and biological roles.

Homo polysaccharide

b. Heteropolysaccharide

Polymer of peptidoglycan

Examples
 disaccharides
 maltose
 isomaltose
 lactose
 sucrose
 oligosaccharides
 not usually free, but covalently linked to protein or lipid
"glycoconjugates"
 mannose very common
 usually very branched
 modified sugars very common, especially w/ charges
 mucins, proteoglycans
 polysaccharides
 energy storage - 1 large soluble

 molecule better than 1000's of small ones
starches
 amylose: glc's linked by a(1,4) bonds
 chains form helices - open center
 amylopectins: a(1,4) chains plus a(1,6) branches (~20 - 24
residues)
 more soluble, why?
 glycogen:
 like amylopectin but more branches (~10 - 12 residues)
 structure
 cellulose: glc's linked by b(1,4) bonds
 flat sheets, insoluble, why?
 chitin: glcNAc linked by b(1,4) bonds

reducing vs. nonreducing ends
• A reducing sugar is any sugar that is capable of
acting as a reducing agent because it has a
free aldehyde group or a free ketone group.
• All monosaccharides are reducing sugars,
along with some dissacharides,
oligosaccharides, and polysaccharides
• carbon which has a free aldehyde or ketone

group is called as reducing, whereas, carbon
not having free aldehyde or ketone group is
called as non-reducing

reducing vs. nonreducing ends

Contoh Soal KH :
 Sebutkan dan jelaskan fungsi KH pada mahluk hidup !
 Apakah yang saudara ketahui tentang chiral molecule ? Jelaskan dan
beri contoh !
 Apakah yang saudara ketahui tentang isomer struktural ? Berikan
contohnya !
 Sebutkan dan jelaskan macam-macam isomer optik serta berikan
contoh masing-masing !
 Sebutkan dan jelaskan klasifikasi KH berdasarkan jumlah sakarida
penyusunnya, serta berikan contoh masing-masing !
 Sebutkan perbedaan struktur antara sukrosa, laktosa dan maltosa !
 Sebutkan perbedaan struktur antara selulosa dan amilum !
 Sebutkan perbedaan struktur antara selulosa dan peptidoglikan !
 Apakah yang saudara ketahui tentang gula reduksi ? Jelaskan serta
berikan contohnya !

3/29/2020 62 Nutrisi

Biokim 3 - Bu Asih - KARBOHIDRAT

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Carbohydrate

Kuliah Biokima Dasar Minggu III

(the word “saccharide” is derived

Kuliah Biokima Dasar Minggu III

II.OLIGOSACCHARIDES ( 2-10 MONOMER)

TRISACCHARIDES C18H32O16 RAFFINOSE (F-GL-GAL)

Kuliah Biokima Dasar Minggu III

HEXOSE (C6H10O5) X STARCH

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar

Kuliah Biokima Dasar Minggu III

 H. Emil Fischer, a German chemist, developed the

Kuliah Biokima Dasar Minggu III

 monosaccharide can be divided into two

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar

 Max possible number of optical isomers of

 There is an additional asymmetric carbon atom and thus

Kuliah Biokima Dasar

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

• carbon which has a free aldehyde or ketone

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar Minggu III

Kuliah Biokima Dasar

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