BIOCHEMISTRY (1)
handed.
CARBOHYDRATES
Biochemistry – the study of the chemical substances found in
living organisms and the chemical interactions of these - the reflection of an object in a mirror
substances with each other.
Biochemical substances – are substances found within a
living organism
a. Bioinorganic substances – do not contain carbon (water
70%; inorganic salts: 5%)
b. Bioorganic substances – contain carbon (protein: 15%;
lipids: 8%; carbohydrates: 2%; nucleic acids: 2%)
CARBOHYDRATES
- The most abundant bioorganic molecule on Earth.
- Green plants produce carbohydrates via photosynthesis.
- Two main uses of carbohydrates in plants: (a) in cellulose
serve as structural elements (b) in starch provide energy
reserve.
Functions
a. Carbohydrate oxidation provides energy
b. Carbohydrate storage, in the form of glycogen provides a
short-term energy reserve.
c. Carbohydrates supply carbon atoms for the synthesis of
other bioorganic substances (protein etc.)
d. Carbohydrates form part of the structural framework of
DNA and RNA molecules.
e. Carbohydrates linked to lipids are structural components
of cell membrane;
f. Carbohydrates linked to proteins function in a variety of
cell-cell and cell-molecule recognition processes.
Classifications
Carbohydrate – a polyhydroxy aldehyde, a polyhydroxy
ketone or a compound that yields polyhydroxy aldehyde or
polyhydroxy ketone upon hydrolysis.
I. Monosaccharide – a carbohydrate that contains a single
polyhydroxy aldehyde or polyhydroxy ketone unit. ex.
glucose (a polyhydroxy aldehyde) and fructose
(polyhydroxy ketone)
- water soluble, white, crystalline solids
II. Oligosaccharide – a carbonate that contains two
monosaccharide units covalently bonded to each other.
Ex. disaccharides – contains two-ten monosaccharide
units covalently bonded to each other. ex. sucrose (table
sugar) and lactose (milk sugar).
III. Polysaccharide – a polymeric carbohydrate that contains
many monosaccharide units covalently bonded to each
- only monosaccharides with 3 to 7 carbon atoms are
other. ex. cellulose and starch.
Chirality: Handedness in Molecules
- Monosaccharides are the simplest form of carbohydrates.
- they mostly exist in two forms: left-handed; right-
Mirror Images
a. Superimposable mirror images – mirror images that
coincide at all points when the images are laid upon
each other.
b.Nonsuperimposable mirror images – mirror images
where not all points coincide when the images are
laid upon each other. (exist in left and right-handed
forms)
Chirality
Chiral center - an atom in a molecule that has four
different groups tetrahedrally attached to it.
a. Chiral molecule – a molecule whose mirror images
are not superimposable; possess handedness (ex.
human hand, bromochloriodomethane,
glyceraldehyde)
b.Achiral molecule – mirror images are
superimposable; do not possess handedness
- chiral centers within molecules are often denoted by a
small asterisk.
Stereoisomerism
- same molecular and structural formula but differ in
the orientation of atoms in space.
- two major features that generate stereoisomerism; (a)
presence of a chiral center in a molecule (b)
presence of structural rigidity in a molecule
(caused by restricted rotation about chemical
bonds)
- divided into two types:
a. Enantiomers: molecules are nonsuperimposable (ex.
left and right-handed molecules w/ a single chiral
center)
b.Diastereomers: molecules are superimposable (cis-
trans isomers)
b.1. Epimers – are diastereomers whose molecules
differ only in the configuration at one chiral center.
Fischer Projection Formula
- a two-dimensional structural notation for showing the
spatial arrangement of groups about chiral centers
in molecules.
- a chiral center is represented as the intersection of
vertical and horizontal lines.
----------------------------------------------------
Classification of Monosaccharides
commonly found in nature: triose: three-carbon
monosaccharide; tetroses: four-carbon; pentoses:
five-carbon; hexoses: six-carbon monosaccharide.
 -
Aldose: a monosaccharide that contains aldehyde
functional group. ex. six-carbon monosaccharide w/ an Characteristics of Polysaccharides
aldehyde functional group: aldohexose
- Ketose: a monosaccharide that contains ketose - are often called glycans (an alternate name for a
functional group. ex. five-carbon monosaccharide w/ a polysaccharide)
ketone functional group: ketopentose
Important parameters that distinguish various
- Sugar is a general designation for either a mono or
polysaccharides from each other:
disaccharide.
a. The identity of the monosaccharide repeating
Biochemically Important Monosaccharides
unit(s) in the polymer chain.
 Triose: D-glyceraldehyde, dihydroxyacetone Homopolysaccharide: only one type of
 D-forms of: glucose and galactose (aldohexose), monosaccharide monomer is present)
fructose, and ribose (ketohexose) b. The length of the polymer chain.
c. The type of glycosidic linkage between
All are water soluble, white crystalline solids. monomer units.
D-Glyceraldehyde and Dihydroxyacetone d. The degree of branching of the polymer
chain.
- the simplest of the mono, are important intermediates in
the process of glycolysis. Only d-glyceraldehyde is a Storage Polysaccharide
chiral molecule. -A polysaccharide that is a storage form for
D-Glucose monosaccharides and is used as energy source in
cells.
- the most abundant in nature and the most important from I. Starch – a homopolysaccharide containing
a human nutritional standpoint. only glucose monosaccharide units. It is the
energy-storage polysaccharide in plants.
D-Galactose
Two (2) different polyglucose polysaccharides
- differ from d-glucose only in the configuration of -OH
and -H group on carbon 4. a. Amylose – a straight-chain glucose polymer, 15-
- A free monosaccharide 20% of the starch
- Synthesized from glucose in mammary glands for use in b. Amylopectin – a branched glucose polymer, 80-
lactose 85% of the starch
D-Fructose
II. Glycogen – a polysaccharide containing only
- Biochemically the most important ketohexose. Also glucose units. It is the glucose storage
known as levulose and fruit sugar polysaccharide in humans and animals
(sometimes referred to as animal starch).
D-Ribose
Structure Polysaccharides
- A pentose; a component of a variety of complex
molecules, including RNA and energy-rich compounds -A polysaccharide that serves as a structural element
such as ATP. in plant cell walls and animal exoskeletons.
I. Cellulose – the most abundant naturally
occurring polysaccharide
Haworth Projection Formula II. Chitin – functions to give rigidity to the
exoskeletons of crabs, lobsters, insects, and
- A two-dimensional structural notation that specifies the other arthropods.
three-dimensional structure of a cyclic form of a
Acidic Polysaccharide
monosaccharide
-A polysaccharide with a disaccharide repeating unit
Reactions of Monosaccharides
in which one of the disaccharide components is an
I. Oxidation to Produce Acidic Sugars amino sugar and one or both disaccharide
II. Reduction to Produce Sugar Alcohols components has a negative charge due to sulfate
III. Glycoside Formation group or carbonyl group.
IV. Phosphate Ester Formation I. Hyaluronic Acid – contains alternating
V. Amino Sugar Formation residues of N-acetyl-β-D-glucosamine and D-
glucuronic acid.
--------------------------------------------------------- II. Heparin – it helps prevent blood clots.
 Glycolipids and Glycoproteins: Cell Recognition
Glycolipid – a lipid molecule that has one or more
carbohydrate (or carbohydrate derivative) units covalently
bonded to each other.
Glycoprotein – a protein molecule that has one or more
carbohydrate (or carbohydrate derivative) units covalently
bonded to it.
Natural sugar – a sugar naturally present in whole foods.
Refined sugar – a sugar that has been separated from its
plant source.