Carbohydrate

Dian Agung Pangaribowo

Materi Perkuliahan

• Definisi dan klasifikasi karbohidrat

• Konfigurasi monosakarida: Proyeksi Fischer; Sistem D dan L
• Konfigurasi aldosa
• Struktur siklik monosakarida
• Pembentukan hemiasetal
• Anomer
• Konformasi monosakarida
• Mutarotasi
Introduction
Honey : a mixture of the two simple
sugars, fructose and glucose
Definition
History :
• Glucose (the first carbohydrate to be obtained pure)

• C6H12O6  Carbohydrate = “hydrate of carbon” C6(H2O)6

Now :
Carbohydrates : polyhydroxy aldehydes and ketones or substances that
hydrolyze to yield polyhydroxy aldehydes and ketones.
They exist primarily in their hemiacetal or acetal forms
Definition
 Classification
Simple Sugar / Monosaccharides
can’t be converted into smaller sugars by hydrolysis
Ex: Glucose, fructose
Carbohydrate
Complex carbohydrates
made of two or more
simple sugars linked
together
• Disaccharides :
hydrolysis  2 molecules of
monosaccharide
• Trisaccharides :
hydrolysis  3 molecules of
monosaccharide
• Oligosaccharides :
hydrolysis  3–10 molecules of
monosaccharide
• Polysaccharides :
hydrolysis  large number of
molecules of monosaccharides (>10)
Classification
Monosaccharides - Classification
Classified according to:
(1) the number of carbon atoms present in the molecule
Monosaccharide containing 3 C : triose 4 C : tetrose
5 C : pentose 6 C : hexose

(2) whether they contain an aldehyde or keto group

• Monosaccharide containing an aldehyde group : aldose
• Monosaccharide containing a keto group : ketose
Monosaccharides - Classification
Problem 1
 Monosaccharides - The D and L Notation
• In Fischer projections : the carbonyl group is always placed on top (in the case of
aldoses) or as close to the top as possible (in the case of ketoses).

OH group attached to the bottom-most asymmetric carbon

• on the right  D-sugar.
• on the left  L-sugar
Configurations
of Aldoses
Configurations of Aldoses

• Diastereomer, Enantiomer, Meso Compound ??

• Epimers : Diastereomers that differ in configuration at only one asymmetric
carbon
Problem 2
Draw D-talose, the C2 epimer of D-galactose
Hemiacetal Formation

• Aldehydes and ketones + alcohols, in the presence of an acid catalyst 

acetals
Cyclic Structure of Monosaccharides
• If the aldehyde group and the hydroxyl group are part of the same
molecule, a cyclic hemiacetal results
• Cyclic hemiacetals are particularly stable if they result in five- or six-
membered rings
• Five- and six-membered cyclic hemiacetals are often more stable than
their open-chain forms.
Cyclic Structure of Monosaccharides
 Draw Haworth structures

1. Lay down the Fischer projection: 2. Rotate the C4-C5 bond to put the C5 – OH
right  down and left  up in place. (For a D sugar, the CH2OH goes
up)
 Draw Haworth structures

3. Close the ring, and draw the final hemiacetal. The hydroxyl group on C1 can
be either up or down.

• α : -OH is on the opposite side of the ring from the -CH2OH group at C5
• β : -OH is on the same side of the ring from the -CH2OH group at C5
 Problem 3

• Draw the Haworth projection for the cyclic structure of D-mannose by laying
down the Fischer projection (α-D-mannopyranose)
 Anomer

• Anomers : two sugars that differ in configuration only at the carbon

that was the carbonyl carbon in the open-chain form

• This carbon is called the anomeric carbon, easily identified as the only
carbon atom bonded to two Oxygens

• The α anomer has the -OH trans to the CH2OH group and the β anomer
has the -OH cis to the CH2OH group.
Mutarotation

• Mutarotation : A slow change in optical rotation to an equilibrium

value
• Pure α-D-glucopyranose has a melting point of 146 °C and a
specific rotation [α]D = +112.2
• Pure β-D-glucopyranose has a melting point of 148 –155 °C and a
specific rotation [α]D = +18.7
• When a sample of either pure anomer is dissolved in water, the
optical rotation slowly changes and ultimately reaches a
constant value of +52.6
Mutarotation
TERIMA KASIH