amino acids are the building blocks of proteins. the general structure of amino acids includes an...

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Page 1: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable
Page 2: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group , an α-carboxylate group and a variable side chain (R) .

Page 3: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

Examples of the Biological significance of amino acids ;Although over 200 different amino acids occur in nature only about

one tenth of these occur in proteins , indicating other biological functions performed by these small organic molecules;

1- They are the building blocks of peptides and proteins.2- As Precursors. Many biologically important molecules are derivates of amino

acids. For exampleTyrosine is the precursor of the hormone thyroxine and the skin pigment melanin, Tyrosine is also the precursor of a compound abbreviated as DOPA (dihydroxy-phenylalanine) . It acts as a neurotransmitter, i.e., trasnmission of impulses in the nervous system, Tryptophan is the precursor of a vitamin named nicotinic acid (B3).

3-As Source of Sulphur. Derived from the sulfur containing amino acids.4- Amino acids are involved in many metabolic pathways such as in

Gluconeogenesis where it is involved in glucose synthesis.

Page 4: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable
Page 5: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable
Page 6: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

1- Optical activity;

All amino acids show optical activity except for glycine , the rest of the amino acids contain at least one asymmetrical carbon atom

What is an asymmetrical carbon atom ? It is a carbon atom that is attached to four different chemical groups(four different substituted groups).

Why does glycine lack optical activity? Since its” R-group” is a Hydrogen atom thus its α-carbon atom is not asymmetrical.

Page 7: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

What does possessing optical activity mean? It means that the amino acid in solution can be present in two isomers;

The (dextrarotatory)(+) isomer which has the ability to rotate the plane of polarized light to the right.

The (laevorotatory)(-) isomer which has the ability to rotate the plane of polarized light to the left.

So both isomers can rotate the plane of polarized light by the same magnitude but in opposite directions.

Page 8: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

2- Acid-Base properties of amino acids;All amino acids contain at least two ionizable

groups the α-amino group and the α-carboxyllic group ,some contain an additional acidic or basic group in their side chain ,which are responsible for the amino acids , acid- base behaviour.

As a result of their ionizability the following equilibrium reaction can be written;

R-COOH R-COO- + H+

R-NH2 R-NH3 +

Page 9: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

Since these reactions are reversible this indicates that they can act as acids (as demonstrated by the forward reaction) or as bases (as demonstrated by the reverse reaction) which explains the acid-base behavior and thus the Amphoteric property of amino acids.

What is the Zwitterions form ?

All neutral amino acids are present in the Zwitterions form at physiological pH (around 7.4) the carboxyl group will be unprotonated and the amino group will be protonated.

Page 10: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

Amphoteric properties of amino acids; amino acids due to the presence of their ionizable α-amino and α-carboxylic group can act sometimes as acids and sometimes as bases depending on the pH of their media .

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Page 11: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

In solutions more basic than the pI of the amino acid, the amino group —NH3+ in the amino acid donates a proton.

In solution more acidic than the pI of the amino acid, the carboxylic group COO- in the amino acid accepts a proton.

Thus behaving sometimes as an acid and other times as a base depending on the pH of the solution.

Page 12: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

a)Polarity of amino acids;Since amino acids are present in the Zwitterions form at

physiological pH.Where it carries a +ve charge on the α-amino group and a –ve charge on the α-carboxylic group , thus creating two opposite chargesOn both sides of the molecule thus showing polar properties.

b)Isoelectric point pI ;It is that pH at which the amino acid net electrical charge is equal to zero ,and

thus cannot move in an electrical field.

Page 13: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

3-Ultraviolet Absorption Spectrum of Aromatic amino acids;

The aromatic amino acids tryptophan , tyrosine , histidine and phenyl alanine absorb ultraviolet light at 280nm ,which explains the absorption of proteins at 280nm.

Page 14: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

Amino acids can be present in two Configurations the L-isomer and the D-isomer which are mirror images , which differ in the arrangement of the chemical groups around the α-carbon atom.

All amino acids in proteins are in the L-configuration , L-amino acids.

Page 15: Amino acids are the building blocks of proteins. The general structure of amino acids includes an α-amino group, an α-carboxylate group and a variable

Physical properties of amino acids;1-Amino acids are mainly water soluble which is explained by its polarity and

the presence of charged groups. They are soluble thus in polar solvents and not soluble in non-polar solvents.

2-They have a high melting point reflecting the high energy needed to break the ionic forces maintaining the crystal lattice.

It is important to note that the general properties of amino acids is shared by all the amino acids and is in many cases contributed by its α-amino and α- carboxyl group . Amino acids can posses other specific properties dictated by they unique side chain.