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Amino Acids
Amino Acids are the building units of proteins. Proteins are
polymers of amino acids linked together by what is called “
Peptide bond”.
 There are about 300 amino acids occur in nature. Only 20
of them occur in proteins. (Standard amino acids)
Amino Acids are named mostly on the basis of their sources. (trivial
names)
Asparagine was first found in asparagus, and glutamate in wheat
(gluten).
Naming and numbering of amino acids
Each amino acid has 4 different groups attached to α-
carbon (which is C-atom next to COOH). These 4 groups
are :
 Amino group
 COOH group
 Hydrogen atom and side
 Chain (R)
R
Amino acids differs in terms of “R” group.
This group affect the nature, solubility and interactions of amino acids.
Structure of amino acids
Chiral carbon/asymmetric center
If a carbon atom is bonded to four different groups it is called as the
asymmetric or chiral carbon.
The α-carbon of amino acids is attached to four different chemical
groups is a chiral or optically active carbon atom.
Glycine is the exception.
Chiral carbon Achiral carbon
Optical properties of amino acids
Stereoisomers
 Chiral carbon can rotate the plane polarized light in to two
directions either in right or to left direction and generate
stereoisomers.
 Those amino acids which rotate plane polarized light in
right direction are called dextro-rotatory, dextro = right
(D) and those rotating light in left are levo-rotatory, levo =
left (L).
How to write the structure of D and L amino acids???
 The reference structure is glyceraldehyde.
Almost all amino acids in human body exist in L-configuration
Enantiomers
 The stereoisomers which are non-superimposable mirror
images of each other are called enantiomers.
 D and L forms of the amino acids are enantiomers.
Chiral carbon
Optical rotation
Stereoisomers
Non-superimposable mirror images
Of 20 amino acids two amino acids have sulfur in side chain
 Cysteine and Methionine.
 What is cystine?
 Only Cysteine form disulfide bonds methionine cannot.
Some features of neutral amino acids
Only one amino acid has achiral alpha carbon
Glycine
Neutral Sulfur containing amino acids:
Cysteine and Methionine. What is cystine?
Neutral, hydroxyl group containing amino acids:
Serine, Tyrosine and Threonine
Amino acids with amide group in side chain:
They are amide forms of aspartate and glutamate in which side chain
COOH groups are amidated.
Amino acids with aromatic side chain
Phenyl alanine: It’s alanine in which one hydrogen of CH3 is
substituted with phenyl group. So it’s called
phenyl alanine
Tyrosine:
Tryptophan: indole ring
Proline is an imino acid not amino acid
III- Classification on basis of nutritional value:
1- Essential amino acids: These amino acids can’t be formed in
the body and so, it is essential to be taken in diet. Their deficiency
affects growth, health and protein synthesis.
2- Non essential amino acids: These are the rest of amino acids
that are formed in the body in amount enough for adults and
children. They are the remaining 10 amino acids.
3- Conditionaly essential or semiessential amino acids: These
are formed in the body but not in sufficient amount for body
requirements especially in children.
 Hydroxylysine and hydroxyproline, are found in the collagen
and gelatin proteins.
 γ-Carboxyglutamic acid is the part of blood clotting protein
prothrombin.
 N-methyllysine is a constituent of myosin.
Sone amino acids are not the part of proteins???
 Ornithine and citrulline act as the intermediates in the urea
cycle
Uncommon amino acids
Simple monoamino monocarboxylic amino acid have weak
acidic and weak basic groups within a single molecule.
Some times side chain contain additional ionizable groups which
also act as acid and base.
Acid-Base properties of amino acids
Any protonated specie can donate its proton if it is present
in the solution whose pH is either equal to the pKa or
greater than pKa of that specie.
• pKa is an equilibrium constant.
• pH is an indication of hydrogen ion content in a
solution
22
Isoelectric point (pI)
The pH at which the amino acid exists largely in a neutral, zwitterionic
form (amphoteric molecule).
pI = 1/2 (pKa1 + pKa2)
For the simplest amino acid, , pKa1= 2.34 and pKa2 =
9.6, pI = 5.97
Titration curve of monoamine and monocarboxylic acid
amino acid
Acid can donate proton when pH of
system becomes equal to or greater than
pKa of acid.
pKa of –COOH = 2.34
pKa of –NH3+ = 9.60
Titration curve of amino acids having acidic side chain
pK1 of –COOH = 2.19
pK2 of –NH3+ = 9.67
pKr (side chain -COOH) = 4.25
pI =
pKa1 + pKa3
2
pI = 2.7
Isoelectric point (pI) of acidic amino acids
Titration curve of amino acids having basic side chain
pK1 of –COOH = 1.82
pK2 of –NH3+ = 9.17
pKr (side chain -NH) = 6.0
pI =
pKa2 + pKa3
2
pI = 9.7
Isoelectric point (pI) of basic amino acids
Can exist as a positive ion if the solution is more acidic than its pI
Can exist as a negative ion if the solution is more basic than its pI
ACIDIC AND BASIC PROPERTIES OF AMINO
ACIDS
• Amino acids in aqueous solution contain weakly
acidic α-carboxyl groups and weakly basic α-amino
groups.
• Thus can act as buffers.
• pH = pKa + log [A-]/[HA]

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1711607810537_3- Amino Acids.ppt56tyyyyy

  • 1. Amino Acids Amino Acids are the building units of proteins. Proteins are polymers of amino acids linked together by what is called “ Peptide bond”.  There are about 300 amino acids occur in nature. Only 20 of them occur in proteins. (Standard amino acids)
  • 2. Amino Acids are named mostly on the basis of their sources. (trivial names) Asparagine was first found in asparagus, and glutamate in wheat (gluten). Naming and numbering of amino acids
  • 3. Each amino acid has 4 different groups attached to α- carbon (which is C-atom next to COOH). These 4 groups are :  Amino group  COOH group  Hydrogen atom and side  Chain (R) R Amino acids differs in terms of “R” group. This group affect the nature, solubility and interactions of amino acids. Structure of amino acids
  • 4.
  • 5. Chiral carbon/asymmetric center If a carbon atom is bonded to four different groups it is called as the asymmetric or chiral carbon. The α-carbon of amino acids is attached to four different chemical groups is a chiral or optically active carbon atom. Glycine is the exception. Chiral carbon Achiral carbon Optical properties of amino acids
  • 6. Stereoisomers  Chiral carbon can rotate the plane polarized light in to two directions either in right or to left direction and generate stereoisomers.  Those amino acids which rotate plane polarized light in right direction are called dextro-rotatory, dextro = right (D) and those rotating light in left are levo-rotatory, levo = left (L).
  • 7. How to write the structure of D and L amino acids???  The reference structure is glyceraldehyde. Almost all amino acids in human body exist in L-configuration
  • 8. Enantiomers  The stereoisomers which are non-superimposable mirror images of each other are called enantiomers.  D and L forms of the amino acids are enantiomers. Chiral carbon Optical rotation Stereoisomers Non-superimposable mirror images
  • 9.
  • 10.
  • 11.
  • 12.
  • 13.
  • 14. Of 20 amino acids two amino acids have sulfur in side chain  Cysteine and Methionine.  What is cystine?  Only Cysteine form disulfide bonds methionine cannot.
  • 15.
  • 16. Some features of neutral amino acids Only one amino acid has achiral alpha carbon Glycine Neutral Sulfur containing amino acids: Cysteine and Methionine. What is cystine? Neutral, hydroxyl group containing amino acids: Serine, Tyrosine and Threonine Amino acids with amide group in side chain: They are amide forms of aspartate and glutamate in which side chain COOH groups are amidated.
  • 17. Amino acids with aromatic side chain Phenyl alanine: It’s alanine in which one hydrogen of CH3 is substituted with phenyl group. So it’s called phenyl alanine Tyrosine: Tryptophan: indole ring Proline is an imino acid not amino acid
  • 18. III- Classification on basis of nutritional value: 1- Essential amino acids: These amino acids can’t be formed in the body and so, it is essential to be taken in diet. Their deficiency affects growth, health and protein synthesis. 2- Non essential amino acids: These are the rest of amino acids that are formed in the body in amount enough for adults and children. They are the remaining 10 amino acids. 3- Conditionaly essential or semiessential amino acids: These are formed in the body but not in sufficient amount for body requirements especially in children.
  • 19.  Hydroxylysine and hydroxyproline, are found in the collagen and gelatin proteins.  γ-Carboxyglutamic acid is the part of blood clotting protein prothrombin.  N-methyllysine is a constituent of myosin. Sone amino acids are not the part of proteins???  Ornithine and citrulline act as the intermediates in the urea cycle Uncommon amino acids
  • 20. Simple monoamino monocarboxylic amino acid have weak acidic and weak basic groups within a single molecule. Some times side chain contain additional ionizable groups which also act as acid and base. Acid-Base properties of amino acids
  • 21. Any protonated specie can donate its proton if it is present in the solution whose pH is either equal to the pKa or greater than pKa of that specie. • pKa is an equilibrium constant. • pH is an indication of hydrogen ion content in a solution
  • 22. 22 Isoelectric point (pI) The pH at which the amino acid exists largely in a neutral, zwitterionic form (amphoteric molecule). pI = 1/2 (pKa1 + pKa2) For the simplest amino acid, , pKa1= 2.34 and pKa2 = 9.6, pI = 5.97
  • 23. Titration curve of monoamine and monocarboxylic acid amino acid Acid can donate proton when pH of system becomes equal to or greater than pKa of acid. pKa of –COOH = 2.34 pKa of –NH3+ = 9.60
  • 24.
  • 25.
  • 26. Titration curve of amino acids having acidic side chain pK1 of –COOH = 2.19 pK2 of –NH3+ = 9.67 pKr (side chain -COOH) = 4.25
  • 27. pI = pKa1 + pKa3 2 pI = 2.7 Isoelectric point (pI) of acidic amino acids
  • 28. Titration curve of amino acids having basic side chain pK1 of –COOH = 1.82 pK2 of –NH3+ = 9.17 pKr (side chain -NH) = 6.0
  • 29. pI = pKa2 + pKa3 2 pI = 9.7 Isoelectric point (pI) of basic amino acids
  • 30. Can exist as a positive ion if the solution is more acidic than its pI Can exist as a negative ion if the solution is more basic than its pI
  • 31. ACIDIC AND BASIC PROPERTIES OF AMINO ACIDS • Amino acids in aqueous solution contain weakly acidic α-carboxyl groups and weakly basic α-amino groups. • Thus can act as buffers. • pH = pKa + log [A-]/[HA]