Complex Carbohydrates

Pharm 271: Phytochemistry

Michael Kwesi Baah

 Learning Outcome
Define carbohydrates?
Types of Carbohydrates
Sources of carbohydrates
Carbohydrate metabolism
Production of commercial carbohydrates

www.knust.edu.gh

3
 What Are Carbohydrates?
• Molecule of carbon(C), hydrogen(H) and
oxygen(O)
• In general, H:O ratio is 2:1) in carbohydrates
• Empirical formula Cm(H2O)n (m may be
different from n)
• Empirical formula is true for monosaccharides
(Some exceptions eg deoxyribose of DNA-
empirical formula C5H10O4
TYPES OF CARBOHYDRATES
▪ Carbohydrate, synonym of 'saccharide’
▪ Includes sugars, cellulose, starch
▪ Saccharides divided into chemical groups:
monosaccharides, disaccharides, polysaccharides
▪ Monosaccharides and disaccharides have
lowest molecular weights
▪ Commonly referred to as sugars
▪ Simple carbohydrates, referred to as sugars:
• fructose (fruit sugar)
• dextrose or glucose (corn or grape sugar )
• sucrose (table sugar)
• lactose (milk sugar)
• Monosaccharides, single molecule eg glucose, fructose
(cannot be broken down to simpler sugars)
• Disaccharides sugar consisting of two monosaccharide
units linked together eg sucrose, maltose, lactose
sucrose= glu~ Fruct
maltose= glu~ glu
lactose = glu ~ galactose
www.knust.edu.gh
▪ Higher saccharides are built from
monosaccharides with general formula
(CH2O)n where n >3
▪ Higher /Complex carbohydrates include
everything made of three or more linked
sugars; include cellulose, glycogen, starches
and fibre
 COMPLEX CARBOHYDRATES
POLYSACCHARIDES
• Polysaccharides are large high-molecular
weight molecules constructed by joining
monosaccharide units together by glycosidic
bonds
• Most important polysaccharides: cellulose,
glycogen and starch
• All are polymers of glucose
CELLULOSE
• A polymer of glucose
• Cellulose has the formula (C 6 H 10 O 5) n
where n ranges from 500 to 5,000
• Partial hydrolysis of cellulose gives cellobiose?
• Glucose units in cellobiose joined by beta-
glycoside bonds between C-1 and C-4 sites of
adjacent sugars

www.knust.edu.gh
The glucose units in cellulose are linked in a
linear fashion
The beta-glycoside bonds permit these chains to
stretch out
The conformation is stabilized by intramolecular
hydrogen bonds

www.knust.edu.gh

10
CELLULOSE REACTIONS
Cellulose is broken down chemically into its
glucose units by treating it with concentrated
mineral acids at high temperature

www.knust.edu.gh
 CELLULOSE ASSAY
• Dissolve the material suspected of
containing cellulose in 17.5% solution of
sodium hydroxide at 20°C
• α- cellulose does not dissolve
• Filter and dry
• Acidify the filtrate to precipitates β
cellulose
• Filter and dry
• Filtrate left contains γ cellulose
www.knust.edu.gh
 CELLULOSE BIOSYNTHESIS
• In vascular plants, a system called Rosette Terminal
Complexes (RTCs) have been identified
• RTCs are located on the plasma membrane
• RTCs are proteins containing three known cellulose
synthesizing enzymes called cellulose synthases
• Synthases use UDP-glucose to form the β(1→4)-linked
monomers in cellulose
• Cellulose synthesis starts with:
-chain initiation catalyzed by CesA using sitosterol-
beta-glucoside and UDP-glucose
-Chain elongation catalyzed by cellulose synthase
using UDP-D-glucose precursors
www.knust.edu.gh
Cellulose is mainly used to produce

• Paperboard, paper, wood pulp, cotton

• Cellophane and rayon.
• Biofuels eg. cellulosic ethanol
• As inactive fillers in tablets
• Fibers- (cotton, rayon, linen) in textiles

www.knust.edu.gh

14
 STARCH/ AMYLUM
• Starch, often referred to as amylum
• It is a polymer of a large number of glucose
units joined by glycosidic bonds:
Formula = (C6H10O5)n
• Two types of molecular arrangements
identified in starch:
-The linear and helical amylose
-Highly branched molecules amylopectin

15
amylose

amylopectin

16
 STARCH BIOSYNTHESIS
• Starch is synthesized in plants by first
converting Glu-1-phosphate to ADP-Glu
• The enzyme involved is Glu-1-Phosphate
adenylyltransferase
• Step requires use of ATP
• The enzyme starch synthase adds the ADP-
Glu through 1,4-alpha glycosidic bond to
grow a chain of glucose residues giving an
amylose
• ADP is liberated (to be re-cycled)
17
Amylopectin
• Series of enzymes introduce 1,6-alpha
glycosidic bonds between the amylose
chains that are formed in the initial starch
synthesis
• Process creates the branched amylopectin

18
 GLYCOGEN
Glycogen
The polysaccharide of glucose in the animal
body.
• Glucose molecules in glycogen are joined by
α-glycoside links between C-1 and C-6, as well
as the α- C-1 to C-4 links (found in maltose).

19
 SOURCES OF CARBOHYDRATES
• Polysaccharides are produced by most green
plants
• Large amounts found in potatoes wheat maize
rice, cassava, yam
• Starch is abundant in potatoes, maize, rice and
other cereals.
• Sucrose (table sugar) - source?
• fructose
• Glycogen
• Cellulose

20
 Starch and industry
• Production of starch
• Uses of
Starch
Cellulose
in industry

21
Isomers in carbohydrates

α-D-glucose

β-D-glucose

22