amino acids organic compounds containing both the amine -nh 2 and carboxyl -cooh functional groups....
TRANSCRIPT
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Amino Acids
• Organic compounds containing both the amine -NH2 and carboxyl -COOH functional groups.
• Amine e.g. CH3CH2NH2 ethylamine
• Carboxylic acid e.g. CH3COOH ethanoic acid.
• Simplest amino acid: aminoethanoic acid- glycine if you are a biologist.
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Week 7
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• State the general formula for an α-amino acid as RCH(NH2)COOH.
• State that an amino acid exists as a zwitterion at a pH value called the isoelectric point.
• State that different R– groups in α-amino acids may result in different isoelectric points.
• Describe the acid–base properties of α-amino acids at different pH values.
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Amino Acids
• Naturally occurring amino acids are all α amino acids.
• This means that both the carboxyl and the amino functional groups are on the SAME carbon atom.
• This leads to the general formula on the next slide.
• These compounds are BIFUNCTIONAL since both functional groups act independently of one another.
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General formula of an α-amino acid
R means any organic side chain.
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Structures of some amino acids
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Physical Properties
• White solids• With relatively high melting points glycine
(the simplest) has a melting point of 235°C.
• Normally readily soluble in water• Almost totally insoluble in non-polar
solvents• Soluble in both acids and bases (alkalis).
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Reactions
• The carboxylic acid group is a proton donor:
• CO2H COO- + H+
• The amine group is a proton acceptor (a base):
• -NH2 + H+ –NH3+
• The amino acids tend to exist as ZWITTERIONS. • These are formed when the carboxyl group and
the amine group have undergone an internal acid-base reaction.
• A proton is transferred FROM the acid TO the amine group so that both ends are charged.
• The overall charge is zero because the positive and negative charges cancel each other out.
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Formation of a zwitterion from glycine
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Isoelectric Point
• pH value at which the amino acid exists as a zwitterion.
• Varies from amino acid to amino acid since the inductive effects of the side chains affects the acid and base strengths of different amino acids differently.
• The isoelectric point has an impact on the acid-base behaviour of the amino acids.
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Amphoteric Behaviour
• Amphoteric means can react with both acid and base .
• pH below isoelectric point:• The amino acid is a base and accepts a proton
from the the acid.• The amino acid is a positively charged ion.
• pH above isoelectric point:• The amino acid is an acid and donates a proton to
the base.• The amino acid forms a negatively charged ion.
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Leucine
Isoelectric point pH 5.98
1. Draw the displayed formula of leucine.
2. Show the structure of leucine at pH 5.98, 2.0 and 7.
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Answers
Nearly full displayed formula.
Skeletal zwitterionic form at pH 5.98
-
At pH7 behaves as an acid At pH2 behaves as a base
H+
-
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Acid–base reactions of an amino acid
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Week 7
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• Explain the formation of a peptide (amide) linkage between α-amino acids to form polypeptides and proteins.
• Describe the acid and alkaline hydrolysis of proteins and peptides to form α-amino acids or carboxylates.
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Peptides and Polypeptides
• A peptide linkage is the –CONH- link
• This is formed in a CONDENSATION reaction between two amino acids with the loss of a water molecule.
• A peptide is a compound containing amino acids linked by peptide bonds.
• Dipeptide = 2 amino acids• Tripeptide = 3 amino acids etc.
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Formation of a dipeptide between glycine and alanine
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Alternative reaction of alanine and glycine
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Peptides and Polypeptides
• A polypeptide is a long chain of amino acids joined by peptide links.
• A protein is a long polypeptide chain with more than 60 amino acid units.
• A polypeptide with 4 different amino acids.
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Hydrolysis
• The breaking of a bond by reaction with water.• Can be acid or base catalysed.• Acid hydrolysis:• Generally refluxed with aqueous (6mol dm-3) HCl
for 24 hours.• The product is the protonated form of the
constituent amino acids.• Alkaline hydrolysis• Reflux with aqueous sodium hydroxide.• Sodium salt formed.
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Acid hydrolysis of a dipeptide
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Alkaline hydrolysis of a polypeptide chain
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Isomerism
Stereo isomerism –same structural formula but different arrangements of groups in space.
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Week 7
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• Describe optical isomers as non-superimposable mirror images about an organic chiral centre.
• Identify chiral centres in a molecule of given structural formula.
• Explain that optical isomerism and E/Z isomerism are types of stereoisomerism.
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• All molecules have a mirror image – but for most molecules it is the same molecule.
fluoromethane
H
CH F
H
H
CHF
H
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• For some molecules the mirror image is a different molecule (the mirror image is non-superimposable). When this happens the 2 forms of the molecule are described as OPTICAL ISOMERS. Optical isomerism is a form of stereoisomerism.
OH
CH CH3
COOH
OH
CHH3C
HOOC
(-) lactic acid (+) lactic acidin sour milk in muscles
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• Molecules that are optical isomers are called enantiomers.
• Enantiomers have identical chemical and physical properties, except:
• Their effect on plane polarised light;• Their reaction with other chiral molecules.
Many natural molecules are chiral and most natural reactions are affected by optical isomerism.
• In nature, only one optical isomer occurs (e.g. all natural amino acids are rotate polarised light to the left).
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• Light is a form of electromagnetic radiation.
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normal light(waves vibrate in all directions)
plane-polarised light(vibrates in only one direction)
plane-polarised light after clockwise rotation
• The wave vibrations are perpendicular to the direction of travel of the wave.
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• Optical isomers rotate the plane of plane polarised light.
(-)-enantiomer(anticlockwise rotation)
(±)-racemate(no overall effect)
(+)-enantiomer(clockwise rotation)
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• http://www.youtube.com/watch?v=3WZZXPOsPNI&feature=related
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• Left and right hands are an example of non-superimposable mirror images.
Optical Isomerism
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OPTICAL ISOMERISMOPTICAL ISOMERISM
Occurrence another form of stereoisomerism occurs when compounds have non-superimposable mirror images
Isomers the two different forms are known as optical isomers or enantiomers they occur when molecules have a chiral centre a chiral centre contains an asymmetric carbon atom
an asymmetric carbon has four different atoms (or groups)arranged tetrahedrally around it.
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OPTICAL ISOMERISMOPTICAL ISOMERISM
Occurrence another form of stereoisomerism occurs when compounds have non-superimposable mirror images
Isomers the two different forms are known as optical isomers or enantiomers they occur when molecules have a chiral centre a chiral centre contains an asymmetric carbon atom
an asymmetric carbon has four different atoms (or groups)arranged tetrahedrally around it.
There are four different colours arranged tetrahedrally about the carbon atom
2-chlorobutane exhibits optical isomerism because the second carbon atom has four different atoms/groups attached
CHIRAL CENTRES
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Most α amino acids are optically active – having non superimposable mirror image isomers. Exception?
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The butan-2-ol molecule has a chiral carbon
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Optical isomers of CH3CH2CH(NH2)CH3
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Week 7
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Simplified three-dimensional representation of two optical isomers
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TASK Which of the following molecules are optically active?
1) propan-2-ol2) 2-chlorobutane3) 1-chlorobutane4) 3-
methylhexane
5) butanone6) 2-methylbutanoic acid7) butan-2-ol8) 1-chloro-3-methylpentane
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propan-2-ol
NOT OPTICALLY ACTIVE
CH3 CH CH3
OH
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2-chlorobutane CH3 CH CH2 CH3
Cl
OPTICALLY ACTIVE
CH2CH3
CH Cl
CH3
CH2CH3
CHCl
H3C
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1-chlorobutane
NOT OPTICALLY ACTIVE
CH2 CH2 CH2 CH3
Cl
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3-methylhexane
OPTICALLY ACTIVE
CH2 CH CH2 CH2
CH3
CH3CH3
CH2CH2CH3
CH CH2CH3
CH3
CH2CH2CH3
CHCH3CH2
CH3
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butanone
NOT OPTICALLY ACTIVE
C CH2 CH3CH3
O
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propan-2-ol CH3 CH CH3
OH
NOT OPTICALLY ACTIVE
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2-methylbutanoic acid
OPTICALLY ACTIVE
CH3 CH2 CH
CH3
C
O
OH
CH2CH3
CCH3 COOH
H
CH2CH3
CCH3
HHOOC
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butan-2-ol
OPTICALLY ACTIVE
CH3 CH2 CH
OH
CH3
CH2CH3
CCH3 OH
H
CH2CH3
CCH3
HHO
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1-chloro-3-methylpentane
OPTICALLY ACTIVE
CH3 CH2 CH
CH3
CH2 CH2
Cl
CH2CH3
CCH3 CH2CH2Cl
H
CH2CH3
CCH3
HCH2ClCH2
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S carvone (caraway seed) R carvone (spearmint)
O
CH3
H C CH2
H3C
O
CH3
HCH2C
CH3
Caraway Seed has a warm, pungent, slightly bitter flavour with aniseed
overtones.
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S limonene (lemons) R limonene (oranges)
CH3
HCCH2
CH3
CH3
H C CH2
H3C
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Week 7
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E and Z isomers of but-2-ene