5 HELPFUL METHODS OF AMINO ACIDS
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5 USEFUL <strong>METHODS</strong> <strong>OF</strong> <strong>AMINO</strong> <strong>ACIDS</strong><br />
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METHOD#1<br />
Amination of alphabromocarboxylic<br />
acids<br />
provides a straight forward<br />
method for preparing<br />
alpha- amino carboxylic<br />
acids. The bromoacid are<br />
conveniently prepared from<br />
carboxylic acids by reaction<br />
with Br2 + PCl3.
METHOD#2<br />
• By modifying the nitrogen as<br />
a phthalimide salt the<br />
propensity of amines to<br />
undergo multiple substitutions<br />
is removed, and a single clean<br />
substitution<br />
reaction of 1º- and many 2ºalkylhalides<br />
takes place.
METHOD#3<br />
An elegant procedure known<br />
as the Strecker synthesis,<br />
assembles an alpha-amino<br />
acid fromammonia (the amine<br />
precursor), cyanide (the<br />
carboxyl precursor) and an<br />
aldehyde. Thisreaction is<br />
essentially an imino analog of<br />
cyanohydrin formation. The<br />
alpha-amino nitrileformed in<br />
this way can then be<br />
hydrolyzed to an amino acid by<br />
either acid or base catalysis.
METHOD# 4<br />
Resolution The three synthetic<br />
procedures described above<br />
and many others thatcan be<br />
conceived, give racemic amino<br />
acid products. If pure L or D<br />
enantiomers aredesired, it is<br />
necessary to resolve these<br />
racemic mixtures.<br />
A common method of resolving<br />
racemates is by diastereomeric<br />
salt formation with apure chiral<br />
acid or base.
METHOD # 5<br />
Resolution The three synthetic<br />
procedures described above<br />
and many others thatcan be<br />
conceived, give racemic amino<br />
acid products. If pure L or D<br />
enantiomers aredesired, it is<br />
necessary to resolve these<br />
racemic mixtures.<br />
A common method of resolving<br />
racemates is by diastereomeric<br />
salt formation with apure chiral<br />
acid or base.
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