KARBOHIDRAT

Indah Saraswati
 KARBOHIDRAT
• Suatu senyawa organik, polihidroksi aldehid
atau polihidroksiketon
• Ada dua gugus fungsional yang penting :
– Gugus hidroksil
– Gugus keton/aldehid
KLASIFIKASI KARBOHIDRAT
 MONOSAKARIDA
• Memiliki atom karbon 3 sampai 6
• Setiap atom karbon memiliki gugus hidroksil,
keton atau aldehida.
• Setiap molekul monosakarida memiliki 1
gugus keton atau 1 gugus aldehida
– Gugus aldehid selalu berada di atom C pertama
– Gugus keton selalu berada di atom C kedua
 MONOSAKARIDA

H O
C CH2OH

H C OH C O

HO C H HO C H

H C OH H C OH

H C OH H C OH

CH2OH CH2OH

D-glucose D-fructose
 SIFAT MONOSAKARIDA
• Padatan kristal tak berwarna
• Larut dalam air
• Sedikit larut dalam alkohol
• Tidak larut dalam eter, kloroform, benzena
• Rasanya manis
– Fruktosa yang paling manis
 SIFAT KIMIA MONOSAKARIDA
• Sifat mereduksi
• Pembentukan furfural
• Pembentukan osazon
• Pembentukan ester
• Isomerisasi
• Pembentukan glikosida
TATA NAMA
TATA NAMA
ALIFATIK - SIKLIK
ALIFATIK - SIKLIK
 PIRAN vs FURAN
6 CH 2OH 6 CH 2OH

5 O 5 O
H H H OH

4 1 4 1
OH H OH H

OH OH OH H
3 2 1 CHO 3 2

H OH 2 H OH
H C OH
α D glukopiranosa 3 β D glukopiranosa
HO C H

4
H C OH

5
H C OH
6
6 CH2 OH CH 2OH 6 CH2 OH
HO C H H H C OH OH
5 O D - glukosa 5 O
1 1
4 OH H 4 OH H

H H 3 2 H
3 2 OH
OH H OH
H

α D glukofuranosa β D glukofuranosa
 ISOMER
• Enansiomer
• Diastereoisomer
• Epimer
• Anomer
• Lingkar monosakarida
• Radikal fungsi
 ENANSIOMER
• Keisomeran optik dimana isomer yang satu
merupakan bayangan isomer yang lain.
CHO CHO CHO CHO

HC OH HO CH HO CH HC OH

HO CH HC OH HO CH HC OH

HC OH HO CH HC OH HO CH

HC OH HO CH HC OH HO CH

CH 2OH CH 2OH CH2 OH CH2 OH

D(+) glukosa L(-) glukosa D(+) manosa L(-) manosa
 DIASTEREOISOMER
• Keisomeran optik pada monosakarida dimana
isomer yang satu bukan bayangan isomer
yang lain
CHO CHO

HC OH HO CH

HO CH HO CH

HO CH HC OH

HC OH HC OH
D(+) galaktosa D(+) manosa
CH 2OH CH2 OH
EPIMER
REARRANGEMENT ENEDIOL
ANOMER
MUTAROTASI
 LINGKAR MONOSAKARIDA
• Keisomeran monosakarida dimana isomer
yang satu merupakan lingkar enam (piran)
dan satunya lingkar lima (furan)
CH2OH

O H
H

OH H α – D - glukopiranosa
OH OH

CH2OH
H OH

H C OH H
O
OH H
β – D - glukofuranosa
H OH
H OH
 RADIKAL FUNGSI
• Keisomeran aldosa-ketosa dimana isomer satu
mempunyai radikal fungsi aldehida/formil dan
satunya mempunya radikal fungsi
keton/karbonil CHO CH OH 2

HC OH C O

HO CH HO CH

HC OH HC OH

HC OH HC OH

CH 2OH CH 2OH

D - glukosa D - fruktosa
 OKSIDASI SAKARIDA

H O
C CO O H
H C OH H C OH

HO C H
Oksidator
HO C H

H C OH H C OH

H C OH H C OH

CH2OH CH2 O H

D-glucose Asam D-glukonat

 TURUNAN GULA

COOH CH O

CH2OH H C OH H C OH

H C OH HO C H HO C H

H C OH H C OH H C OH

H C OH H C OH H C OH

CH2OH CH2OH COOH

D-ribitol Asam D-glukonat Asam D-glukuronat

 TURUNAN GULA
CH2OH CH 2OH

H O H H O H
H H
OH H OH H

OH OH OH O OH
H NH 2 H N C CH 3
H
a-D-glukosamina a-D-N-asetilglukosamina

Gula amino - gugus amino menggantikan gugus

hidroksil. Sebagai contoh glukosamina.
Gugus amino dapat mengalami asetilasi, seperti pada N-
asetilglukosamina.
 DISAKARIDA
• Klasifikasi :
– Disakarida pereduksi
• Laktosa
• Maltosa
• Selobiosa
– Non pereduksi
• Sukrosa
• Threhalosa
• Klasifikasi :
– Homo disakarida : maltosa
– Heterodisakarida : sukrosa
 DISAKARIDA
• Tiga ikatan glikosidik secara alami :
– Hubungan 1-4’ : karbon anomerik terikat pada
oksigen C4 monosakarida kedua
– Hubungan 1-6’ : karbon anomerik terikat pada
oksigen C6 monosakarida kedua
– Hubungan 1-1’ : karbon anomerik dari dua
monosakarida terikat melalui sebuah oksigen
• Homo disakarida
OH + HO O + H2O
CH2 OH CH2 OH

O O H
H H H
H H
OH H OH H

O OH
OH

H OH H OH

maltosa

• Heterodisakarida
OH + HO O + H2O
CH2 OH

O H CH2 OH H
H
O
H
OH
OH H

OH O CH 2 OH

OH
H OH
LACTOSE - GALACTOSEMIA
 POLISAKARIDA
CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O H O H O H H O H
H H H H H
H H H H H
OH H 1 4 OH H 1 OH H OH H OH H
O O O O OH
OH 2
3
H OH H OH H OH H OH H OH
amylose

Plants store glucose as amylose or amylopectin, glucose

polymers collectively called starch. Glucose storage in
polymeric form minimizes osmotic effects.
Amylose is a glucose polymer with a(14) linkages. It
adopts a helical conformation.
The end of the polysaccharide with an anomeric C1 not
involved in a glycosidic bond is called the reducing end.
 CH2OH CH2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH

CH2OH CH2OH 6 CH2 CH2OH CH2OH

H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH
3 2
H OH H OH H OH H OH H OH

Amylopectin is a glucose polymer with mainly a(14)

linkages, but it also has branches formed by a(16)
linkages. Branches are generally longer than shown above.
The branches produce a compact structure & provide
multiple chain ends at which enzymatic cleavage can occur.
 CH2OH CH2OH
H O O
glycogen
H H H
H H
OH H OH H 1
O
OH
O
H OH H OH

CH2OH CH2OH 6 CH2 CH2OH CH2OH

H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH 2
3
H OH H OH H OH H OH H OH

Glycogen, the glucose storage polymer in animals, is

similar in structure to amylopectin. But glycogen has
more a(16) branches.
The highly branched structure permits rapid release of
glucose from glycogen stores, e.g., in muscle during
exercise. The ability to rapidly mobilize glucose is more
essential to animals than to plants.
 CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose
Cellulose, a major constituent of plant cell walls, consists
of long linear chains of glucose with b(14) linkages.
Every other glucose is flipped over, due to the b linkages.
This promotes intra-chain and inter-chain H-bonds and
van der Waals interactions,
that cause cellulose chains
to be straight & rigid, and
pack with a crystalline
arrangement in thick
bundles called microfibrils. Schematic of arrangement of
cellulose chains in a microfibril.
APLIKASI
 CH 2OH
D-glucuronate 6
 H 5 O
6COO H
4 1 O
O H
H 5
H OH H
4 H 1 3 2
OH
H H NHCOCH 3
3 2 O
H OH N-acetyl-D-glucosamine
hyaluronate

Glycosaminoglycans (mucopolysaccharides) are polymers

of repeating disaccharides.
Within the disaccharides, the sugars tend to be modified,
with acidic groups, amino groups, sulfated hydroxyl and
amino groups, etc.
Glycosaminoglycans tend to be negatively charged,
because of the prevalence of acidic groups.
ERYTHROPOIETIN