PHARMACEUTICAL

BIOCHEMISTRY
CARBOHYDRATES
1st semester A.Y. 2024-2025

JHOANA ROZE M. TUNGOL, RPh, MPH

INSTRUCTOR
OBJECTIVES
At the end of the discussion, the students must be able to:

▪Demonstrate knowledge on carbohydrates’ structure,

functions, classification and physicochemical properties.

▪Demonstrate an understanding of the clinical

significance of carbohydrates.
OUTLINE
▪Carbohydrates
▪Chirality
▪Stereoisomerism
▪Classification
▪Monosaccharides
▪Disaccharides
▪Polysaccharides
CARBOHYDRATES
▪Most abundant class
▪Photosynthesis → carbohydrates
▪Cellulose- structural elements
▪Starch- provide energy reserves
▪Dietary intake
FUNCTIONS IN HUMANS
▪Carbohydrate oxidation → energy
▪Carbohydrate storage (glycogen)
▪Carbohydrates supply carbon atoms
▪Carbohydrates as structural framework
▪Carbohydrates linked to lipids
▪Carbohydrates linked to proteins
CARBOHYDRATES
▪CnH2nOn
▪Cn(H2O)n - “hydrate of carbon”
▪PHA / PHK
▪Yielded upon ______________
▪Large functional groups present
▪Classified based on molecular size
CARBOHYDRATES
CnH2nOn

MPIPSANTOS, 2020
CLASSIFICATION OF CARBOHYDRATES:
NO. OF SUGAR UNITS
CLASSIFICATION OF CARBOHYDRATES:
FUNCTIONAL GROUP

Ketose
Aldose
 CLASSIFICATION OF CARBOHYDRATES:
NO. OF CARBONS

Pentose

Hexose
NOMENCLATURE
# Carbons With formyl With carbonyl
3 Aldotriose Ketotriose
4 Aldotetrose Ketotetrose
5 Aldopentose Ketopentose
6 Aldohexose Ketohexose
7 Aldoheptose Ketoheptose
FISCHER PROJECTION FORMULA
▪Two-dimensional structural notation
▪Shows spatial arrangement of groups
about chiral centers in molecules
▪Chiral center is represented as the
intersection, always carbon
FISCHER PROJECTION FORMULA
FISCHER PROJECTION FORMULA
BASIC CONCEPTS TO CHIRALITY
▪Handedness

▪Mirror-Image
▪Superimposable
▪Nonsuperimposable
CHIRALITY
▪Chiral Center
▪Carbon atom with four different groups
attached in a tetrahedral orientation
▪Chiral Molecule
▪not superimposable – have handedness
▪Achiral Molecule
▪Superimposable- do not possess handedness
CHIRAL MOLECULES
STEREOISOMERISM
▪Stereoisomers
▪Isomers that have the same molecular
and structural formulas but differ in
orientation of atoms in space
▪Enantiomers
▪Diastereomers
ENANTIOMERS
▪Mirror images
▪Non-superimposable
DIASTEREOMERS
▪Non-mirror images
▪Non-superimposable
EPIMERS
EPIMERS
HAWORTH PROJECTION FORMULAS

▪two-dimensional structural notation that

specifies the three-dimensional structure
of a cyclic form of a monosaccharide
FISCHER TO HAWORTH PROJECTION

MPIPSANTOS, 2020
CLASSIFICATION OF CARBOHYDRATES

▪Monosaccharides
▪Disaccharides
▪Oligosaccharides
▪Polysaccharides
MONOSACCHARIDES
▪Based on
functional group
▪Aldoses
▪Ketoses

▪Based on the
number of carbon
atoms
 Examples
#C Name Aldose Ketose
(-ose) (-ulose)
2 Diose Hydroxyacetaldehyde -
3 Triose Glyceraldehyde Dihydroxyacetone
Erythrose
4 Tetrose Erythrulose
Threose
Ribose
5 Pentose Arabinose Ribulose
Xylose
Mannose
6 Hexose Glucose (Dextrose) Fructose (Levulose)
Galactose
7 Heptose - Sedoheptulose
8 Octose - Glycero-manno-octulose
9 Nonose - Sialic acid
IMPORTANT MONOSACCHARIDES
Monosaccharide Source Important Information
D-Glyceraldehyde and - Important intermediates of
Dihydroxyacetone glycolysis
Starch, Glycogen Most abundant / important
Glucose Amino Acid, Lactate blood sugar
Pyruvate dextrose
“milk sugar” or “brain sugar”
Galactose Mammary gland
*galactosemia
“fruit sugar”
Fructose Sucrose, Inulin
Sweetest sugar
Ribose Nucleic acid sugar
Arabinose Gum Arabic A. Senegal
Xylose Corn Cob “wood sugar”
DISACCHARIDES
▪Two monosaccharide units
▪Mono + Mono
▪Glycosidic linkage
GLYCOSIDIC BONDS
IMPORTANT DISACCHARIDES
 Glycosidic
Disaccharide Components
Linkage
Sucrose Glu + Fru α,β-1,2
Lactose Glu + Gal β-1,4
Lactulose Fru + Gal β-1,4
Maltose Glu + Glu α-1,4
Trehalose Glu + Glu α-1,1
Cellobiose Glu + Glu β-1,4
Sophorose Glu + Glu β-1,2
IMPORTANT DISACCHARIDES
▪Maltose - 2 D-glucose (𝛂 1,4)
▪malt sugar
▪ Common ingredient in baby foods
▪ Found in malted milk
▪ Brewers Yeast: contains enzymes that hydrolyze barley malt first to
maltose, then to glucose (then fermented to make beer)
IMPORTANT DISACCHARIDES
▪Lactose
▪major sugar in milk
▪important ingredient in
infant formulas
▪Lactase → Gal + Glu

▪Clinical Correlation:
Lactose Intolerance
 IMPORTANT DISACCHARIDES
Cellobiose - 2 D-glucose (𝜷 1-> 4)
▪ obtained from the hydrolysis of cellulose
 IMPORTANT DISACCHARIDES
Sucrose - 𝛂-D-glucose and 𝜷-D-fructose
▪ common table sugar, from sugarcane and
sugar beets
▪ hydrolyzed to provide energy
▪ excess quantities - health problems
▪ Artificial sweeteners
▪ Saccharin - causes cancer in lab
animals
▪ Aspartame (Nutrasweet) - causes
neurological problems
▪ Sucralose (Splenda) - not metabolized
by the body (does not provide
calories)
OLIGOSACCHARIDES
▪Three or more monosaccharide units
Oligosaccharide Components
Raffinose Gal-Glu-Fru
Gentianose Glu-Glu-Fru
Maltotriose Glu-Glu-Glu
Sucralose Glu-Fru-Gal
CLINICAL CORRELATION:
BLOOD TYPES AND OLIGOSACCHARIDES
POLYSACCHARIDES
▪Many monosaccharide units
▪Glycans
▪Identity
▪Homopolysaccharides
▪Heteropolysaccharides
▪Length
▪Glycosidic linkage
▪Branching
STORAGE POLYSACCHARIDES
▪Starch
▪homopolysaccharide
▪Glucose only
▪Energy-storage in plants

▪Amylose
▪Amylopectin
STARCH Amylose
𝛂 (1 -> 4)

Amylopectin

𝛂 (1 -> 4)
&
𝛂 (1 -> 6)
STARCH
Amylose Amylopectin
(B-amylose) (a-amylose)
Structure
Bonds
Percentage
Iodine Test
STORAGE POLYSACCHARIDES
▪Glycogen
▪Homopolysaccharide containing glucose
▪Storage polysaccharide in humans and animals
—> “animal starch”
▪More complex than starch
GLYCOGEN STORAGE DISEASES
GSD Type Other name Enzyme Deficient
Type 0 Glycogen synthase
Type I Glucose-6-phosphatase (Ia)
G-6-translocase (Ib)
Type II a-1,4-glucosidase or Acid Maltase
Type III
Type IIIa
Debranching enzyme (a-1,6-
Type IIIb
glucosidase)
Type IIIc
Type IIId
Type IV Branching Enzyme
Type V Muscle phosphorylase
Type VI Glycogen phosphorylase
Type VII Muscle phosphofructokinase
Type VIII Liver phosphorylase kinase
STRUCTURAL POLYSACCHARIDES
▪Cellulose
▪Structural component of plant cell walls
▪Most abundant
▪Cotton and Wood
▪Not digested by mammalian systems
▪Reagent to dissolve:
STRUCTURAL POLYSACCHARIDES
▪Chitin
▪Similar to cellulose
▪Exoskeletons
▪Crabs, lobsters, shrimp,
insects, and other
arthropods
CHITIN
POLYSACCHARIDES IN CELL WALLS
Prokaryotic cells :
Polysaccharides cross linked
with peptides
▪ Polysaccharide units:
▪ N-acetyl-D-glucosamine (NAG)
▪ N-acetylmuramic acid (NAM) —
exclusively found in prokaryotes
“Peptidoglycan”
 BETA LACTAM ANTIBIOTICS
▪ Mimics the D-Ala-D-Ala peptide terminus, binds to the active site of
the transpeptidase enzyme, thereby inhibiting the cross linking of
NAM-NAG, and ultimately, cell wall synthesis
▪ Active moeity: 𝜷-LACTAM ring
▪ Antibiotics include:
▪ Penicillins
▪ Cephalosporins
▪ Carbapenems
▪ Monobactams
BETA LACTAM ANTIBIOTICS
BETA LACTAM ANTIBIOTICS
BETA LACTAM ANTIBIOTICS
 POLYSACCHARIDES IN CELL WALLS
Plant cells :

▪ Cellulose - “insoluble” fiber (roughage) - binds toxic

substances in food and bile fluid

▪ Pectin - polymer, made up of mostly D-galacturonic

acid
▪ Extracted from plants due to it’s importance as a gelling agent in
yogurt, jams, and jellies.
 POLYSACCHARIDES IN CONNECTIVE TISSUES
▪ GlycosAminoGlycans
▪ At least 1 sugar is an amino sugar
▪ At least 1 negative charge due to the presence of a sulfate or a
carboxyl group

Figure 16.29
Biochemistry, Seventh Edition
© 2012 W.H. Freeman and Company
POLYSACCHARIDES IN CONNECTIVE TISSUES
▪Heparin - blood coagulation
▪Hyaluronic acid - vitreous humor of the eye and
lubrication for the joints
▪Chondroitin sulfate and keratan sulfate - connective
tissues
▪Glucosamine sulfate and chondroitin sulfate - OTC
medications for damaged cartilage
REFERENCES
▪ Stoker, H. (2016) General, Organic and Biological Chemistry
(7th Ed.). Boston, MA, USA : Cengage Learning
▪ Devlin, T. (2011) Textbook of Biochemistry with clinical
correlations (7th Ed.). Hoboken, NJ : John Wiley & Sons
▪ Campbell, MK & S.O. Farrell. (2015) Biochemistry. (8th Ed.).
Thomson Asia Pte. Ltd. : Singapore
▪ Nelson, D., Cox, M. (2008). Lehninger principles of
Biochemistry Fifth Edition. New York: W.H. Freeman and
Company.
▪ Boyer, R. (2006). Concepts in Biochemistry 3rdEdition. New
York: John Wiley & Sons.