Biochemistry

 It is the study of the chemical substances found in living organisms and

the chemical interactions of these substances with each other 
Biochemical Substance

 It is a chemical substance found within a living organism.

 Divided into two groups:
 Bioinorganic Substance – substance that do not contain carbon (more
abundant)
 Bioorganic Substance – substance that contain carbon (less abundant)
Bioinorganic Substances
 Water (about 70%)
 Inorganic Salts (about 5%)
Bioorganic Substance 

 Carbohydrates (2%)
 Lipids (8%)
 Proteins (15%)
 Nucleic Acids (2%)
Functions of Carbohydrates
 Carbohydrate oxidation provides energy
 Carbohydrate storage in the form of glycogen provide short-term energy
 Carbohydrate supply carbon atom for the synthesis of other
biochemical substances (protein, lipids and nucleic acid)
 Carbohydrate form part of the structural framework of DNA and
RNA molecules

Functional Groups
  

Carbohydrate
 It is a polyhydroxy aldehyde, polyhydroxy ketone or a compound that
yields polyhydroxy aldehydes or polyhydroxy ketones upon hydrolysis.
 General Formula CnH2nOn  or Cn(H2O)n

Classification of Carbohydrates Base on Molecular Size

 Monosaccharide
 Disaccharide
 Oligosaccharide
 Polysaccharide
 Monosaccharide – is a carbohydrate that contains a single polyhydroxy
aldehyde or ketone unit. (Fructose and Glucose) 
 Cannot be broken down into simpler unit by hydrolysis reaction
 Have 3 to 7 carbon atoms
 Water soluble, White, Crystalline Solid
 Disaccharide – is a carbohydrate that contains two monosaccharide units
covalently bonded to each other. (Sucrose (table sugar) and Lactose (milk
sugar))
 Hydrolysis of disaccharide produces two monosaccharide units.
 Water soluble, White, Crystalline Solid
 Oligosaccharide – is a carbohydrate that contains three to
ten monosaccharide units covalently bonded to each other.
 “Free” oligosaccharides usually found associated with proteins and lipids
 Complete hydrolysis of oligosaccharide produces several monosaccharide
units
  Ex. Hexasaccharide, Trisaccharide
 Polysaccharide – is a polymeric carbohydrate that contains
many monosaccharide units covalently bonded to each other. (Starch, paper
(cellulose), food, pasta rice etc.)
 Few hundred units to 50,000 units of monosaccharide
 Can also undergo hydrolysis to produce monosaccharide

Chirality: Handedness in Molecules

 Molecules that possess “handedness” exist in two forms “left-handed” and
“right-handed” form
 These two forms are related to each other in the same way that a pair of hands
are related to each other.
 The relationship is that of mirror images
 A left hand and a right hand is a mirror image

Mirror Images
 It is the reflection of an object in a mirror
 Objects can be divided into two classes on the basis of their mirror images
  Superimposable mirror images – images that are coincide at all points when
the images are laid upon each other
 Nonsuperimposable mirror images – are images where not all
points coincide when image is laid upon each other. (All objects
with nonsuperimposable mirror images exist in “left-handed” and “right-
handed” forms)
Chirality/Handedness
 For organic and bioorganic compounds, the structural requirement for
handedness is the presence of a carbon atom that has four different groups
bonded into a tetrahedral orientation single bondedly. 
Chirality
 The handedness-generating carbon atom is called a chiral center.
 A chiral center is an atom in a molecule that has four different group bonded
to it a tetrahedral orientation.
 A molecule that contains chiral center is said to be chiral.
 Chiral molecule – is a molecule whose mirror images are not superimposable
 Achiral molecule – is a molecule whose mirror images are superimposable.
(Does not possess handedness)

  

Handedness using 
Fischer Projection Formulas
  The German chemist Hermann Emil Fischer
(1852-1919) the developer of the two-dimensional system for specifying
chirality, was one of the early greats in organic chemistry. He made many
fundamental discoveries about carbohydrates, proteins, and other natural
products: in 1902 he was awarded the second Nobel Prize in Chemistry.
 A Fischer projection formula is a two dimensional structural  notation for
showing the spatial arrangement of groups about chiral centers in molecules.

Stereoisomerism: 
Enantiomers and Diastereomers
 The left and right-handed forms of a chiral molecule are isomers. 
 Stereoisomers are isomers that have the same molecular and structural
formulas but differ in the orientation of atoms in space
 Stereoisomers can be subdivided into two types: enantiomers and
diastereomers. Enantiomers are stereoisomers whose molecules
are nonsuperimposable mirror images of each other. Left- and right-handed
forms of a molecule with a single chiral center are
enantiomers.  Diastereomers are stereoisomers whose molecules are not
mirror images of each other. Molecules that contain more than one
chiral center can also exist in diastereomeric as well as enantiomeric forms

Stereoisomerism: 
Enantiomers and Diastereomers
   

 What is the importance of handedness, the topic now under discussion, in a

bio- chemical setting such as the human body? In human-body chemistry it is
found that right-handed and left-handed forms of a molecule usually elicit
different responses and that our bodies can normally use only one of the two
forms of a chiral com- pound. Sometimes both forms are biologically active,
each form giving a different response; sometimes both elicit the same
response, but one form's response is many times greater than that of the other;
and sometimes only one of the two forms is biochemically active. For
example, studies show that the body's response to the right- handed form of
the hormone epinephrine is 20 times greater than its response to the left-
handed form. OH 
 All proteins, most fats, and all common carbohydrates are chiral
substances. Monosaccharides, the simplest type of carbohydrates, and the
building block for more complex types of carbohydrates are almost always
"right-handed" molecules. This is because plants, the main dietary sources for
carbohydrates, produce only right-handed monosaccharides. Based on this
observation, it is not correct to assume that "right-handed" is always dominant
over "left-handed" in a biochemical setting. Interestingly, the building blocks
for proteins, amino acids are always left-handed molecules.