BIOCHEM QUIZ NO.

1 REVIEWER

BIOCHEMISTRY- is the study of chemical substances found in living organisms and the chemical
interaction of these substances with each other

- Is the field in which new discoveries are made almost daily

Biochemical Substances – chemical substances found in living organisms.

1. Bioinorganic Substances – substances that do not contain carbon

a. Water – 70 %
b. Inorganic Salts – 5%
2. Bioorganic substances – substances that contain carbon
a. Proteins – 15%
b. Lipids – 8%
c. Carbohydrates – 2%
d. Nucleic Acids – 2%

CARBOHYDRATES (CnH2nOn or Cn(H2O)n)

- Hydrate of carbon
- Are the most abundant class of bioorganic molecules on Earth
- Constitutes about 75% by mass of dry plants materials
- Are produces by green (chlorophyll-containing) plants via photosynthesis
- CO2 and H2O are the reactants and sunlight is the energy source
CO2 + H2O + solar energy chlorophyll lcarbohydrates + O2
- Dietary intake of plants is the major carbohydrate source for humans
- Average human diet – 2/3 carbohydrate by mass
- A polyhydroxy aldehyde and polyhydroxy ketone or a compound that yields polyhydroxy aldehydes or polyhydroxy ketones upon
hydrolysis

Plants have 2 main uses of Carbohydrates:

1. Cellulose – structural element

2. Starch – provides energy reserve for the plants

Functions of Carbohydrates in Humans

1. Carbohydrate oxidation provides energy

2. Carbohydrate storage in the form of glycogen provides short term energy reserve
3. Supply carbon atoms for the synthesis of other biochemical substances
4. Form part of the structural framework of DNA and RNA
5. Carbohydrates linked to lipids are structural components of cell membrane
6. Carbohydrates linked to proteins function in a variety of cell to cell and cell molecule recognition process

Classifications of Carbohydrate based on Molecular Size

1. Monosaccharides
- Carbohydrate that contains a single polyhydroxy aldehyde of a polyhydroxy ketone unit
- Cannot be broken down into simpler units by hydrolysis
- Glucose and fructose
- Have 3 to 7 carbon atoms; 5 and 6 carbon species are especially common
- Pure monosaccharides are water-soluble, white, crystalline solids
2. Disaccharides
- Contains 2 monosaccharides covalently bonded to each other
- Crystalline, water- soluble
- Sucrose and lactose
- Hydrolysis produces 2 monosaccharide units
3. Oligosaccharides
- Oligo Gr. Word “oligos” means small or few
- Contains 3 to 10 monosaccharides covalently bonded to each other
- Free oligosaccharides are seldom encountered and found associated with proteins and lipids
- Produces several monosaccharide molecules
4. Polysaccharides
- Polymeric carbohydrate that contains many monosaccharides covalently bonded to each other
- Varies from a few hundred up to 50,000 units
 - Also undergo hydrolysis
- Cellulose and starch

Handedness

- important property of molecules including carbohydrates

- A form of isomerism
- Exists in 2 forms
a. Left handed
b. Right handed

Mirror Images

- Is the key to understanding handedness

- Reflection of an object in a mirror
a. Superimposable – coincides at all points when images are laid upon another
b. Non-superimposable – not all points coincide when the images are laid upon one another

CHIRALITY

Chiral center – handedness generating carbon atom

- Atom in a molecule that has 4 different groups bonded into a tetrahedral orientation

Chiral molecule – molecule with a chiral center

- Molecule in which mirror image is not superimposable

- Have handedness
- Bromochloroiodomethane – trisubstituted methane molecule
- Optically active

Achiral Molecule – mirror images are superimposable

- Doesn’t possess handedness

- Isopropyl alcohol
- Optically inactive

Guidelines in Determining the Presence or lack of Chiral Center

1. Carbon atom involved in multiple bonds cannot be a chiral center

2. Commonly encountered entities -CH3 and -CH2 in a structural formula never involved chiral center because the presence of 2
or more like hydrogen atoms
3. Carbon atoms in a ring system, if not involved in multiple bonding can be chiral centers

Importance of Chirality

 Right handed epinephrine is 20 times greater than its response to the left-handed form
 Carbohydrates are always right-handed because plants only produce right-handed monosaccharides
 Amino acids are always left-handed

STEREOISOMERISM

Stereoisomers – are isomers that have the same molecular and structural formula but differ in the
orientation of atoms in space

Major Structural Features

1. Presence of chiral center in a molecule

2. Presence of structural rigidity in a molecule – caused by restricted rotation about chemical bonds

2 Types

1. Enantiomers - molecules are nonsuperimposable mirror images of each other

- Left and right-handed forms of a molecule with a single chiral center
- Handedness is determined by the configuration at the highest-numbered chiral center
- Optical isomers
2. Diastereomers – molecules are not mirror images of each other
a. Cis-trans isomers – a phenomenon found in some substituted cycloalkanes and alkenes
 - Results from restricted rotation about chemical bonds
* Is sometimes possible when a ring is present
* is sometimes possible when a double bond is present

b. Most other Diastereomers (2 or more chiral center) – stereoisomerism that results from:

* A mirror-image relationship at one or more chiral center

* The same configuration at one or more chiral center

CONSTITUTIONAL ISOMERS – isomers in which the atoms have different connectivity

1. Skeletal isomers – different carbon and hydrogen atom arrangements

2. Positional isomers – different location of functional groups
3. Functional group isomers – different functional group

Fischer Projection Formula

- Discovered by Hermann Emil Fischer (1852 – 1919)

- Two-dimensional structural notation for showing the spatial arrangement of groups about chiral centers in molecules
- Chiral center is represented as the intersection of the horizontal and vertical line
- Carbon chain is always positioned vertically with the carbonyl group near the top

Interpretations for a printed 3D model of tetrahedral bond

1. Central atom is the plane of the paper

2. 2 bonds (vertical lines) are considered to be directed into the printed page
3. 2 bonds (horizontal lines) are considered to be directed out of the printed page

Epimers – are diastereomers whose molecules differ only in configuration at one chiral center

PROPERTIES OF ENANTIOMERS

Enantiomers exhibit different properties only in 2 areas:

1. Interaction with plane-polarized light

 All light moves through space with a wave motion
 Ordinary light waves (unpolarized light waves) vibrate in all planes at right angles to their direction of travel
 Plane polarized light waves vibrate only in one plane at right angles to their direction of travel
 Polarizer – instrument with lenses or filters containing special types of crystals
- Converts ordinary light into plane-polarized light
 When plane-polarized light is passed through a solution containing a single enantiomer, the plane of the
polarized light is rotated counterclockwise or clockwise depending on the enantiomer
 Polarimeters – instruments used to measure degree of rotation of plane-polarized light by enantiomeric
compounds

Optically active compound – compound that rotates the plane of polarized light

Dextrorotatory compound (+) - an enantiomer that rotates plane-polarized light in a clockwise direction (to
the right)

Levorotatory (-) – chiral compound that rotates the plane of polarized light in a counterclockwise direction

2. Interaction with other chiral substances

a. Enantiomers have identical boiling points, melting points and densities because such properties depend on strength of
intermolecular forces and intermolecular strength does not depend on chirality.
b. A pair of enantiomers have the same solubility in an achiral solvent but different solubility in chiral solvent
c. Rate of extent of reaction of enantiomers with another reactant are the same if the reactant is achiral but differ if the
reactant is chiral\receptor sites for molecules within the body have chirality associated with them

CLASSIFICATIONS OF MONOSACCHARIDES

Triose – 3 carbon monosaccharide

Tetrose – 4 carbon monosaccharide

Pentose -5 carbon monosaccharide

Hexose – 6 carbon monosaccharide

A. Based on the Carbonyl Group

1. Aldose – monosaccharide that contains an aldehyde functional group
- Polyhydroxy aldehydes
- Aldohexose – 6 carbon monosaccharide with aldehyde functional group
2. Ketose – monosaccharide that contains a ketone functional group
- Polyhydroxy ketones
- Ketopentose – 5 carbon monosaccharide with ketone functional group

Sugar

- Latin word saccharum

- Associated with sweetness
- General designation of monosaccharides or disaccharides

Trioses

- Smallest monosaccharides that can exist

a. Glyceraldehyde – aldose
b. Dihydroxyacetone- ketose
- Does not possess a chiral carbon atom

D monosaccharides – important energy source of the body

L monosaccharides – produced in the laboratory cannot be used as an energy source of the body

Aldohexose – 4 chiral carbon atoms

Ketohexose – 3 chiral carbon atoms

BIOCHEMICALLY IMPORTANT MONOSACCHARIDES

1. D-Glyceraldehyde and Dihydroxyacetone

- Simplest of the monosaccharides
- Important intermediates in the process of glycolysis (a series of reactions whereby glucose is converted into
2 or molecules of pyruvate)
2. D-Glucose
- Most abundant in nature and most important from a human nutritional standpoint
- Ripe fruits are a good source of glucose (20-30% glucose by mass)
- Grape sugar, dextrose, blood sugar
- Dextrose (rotates plane polarized light to the right)
- Blood sugar (blood contains dissolved glucose)
- Normal concentration of glucose in human blood (70-100 mg/dL)
- Concentration of 130 mg/dL occurs in the first hour of eating
- Insulin and Glucagon are important in keeping the glucose blood concentration within a normal range
- Abnormal functioning leads to diabetes
3. D-Galactose
- Differ only in the configuration of the OH and H group on Carbon 4 with D-glucose
- Seldom encountered as a free monosaccharide
- Synthesized from glucose in the mammary glands
- Also called brain sugar because it is a component of glycoprotein found in brain and nerve tissues
- Present in the chemical marker that distinguish different types of blood
4. D-Fructose
- Most important ketohexose
- Also called levulose (rotate plane polarized light to the left) and fruit sugar
- Sweetest tasting of all sugars
- Used as a dietary sugar
- From 3rd to 6th carbon D-fructose is identical to D-glucose
5. D-Ribose
- A pentose
- Component or DNA, RNA and ATP
- “deoxy” minus as oxygen