12.

AMINES & AMINO ACIDS

A. Structure & Nomenclature

B. Properties

C. Analysis
Classification of Amines
 Nomenclature
Structure Common name Systematic name
CH3NH2 methylamine methanamine
(CH3)2NH dimethylamine
(CH3)3N trimethylamine
(CH3)2CHNH(CH3) N-methyl-2-propanamine N-methylisopropylamine

C6H5NH(CH2CH3) N-ethylaniline

Br-C6H4NH2 o-bromoaniline
 Interesting Amines

cadaverine
putrescine
pentane-1,4-diamine
butane-1,4-diamine

trimethylamine
 Interesting Amines

2-phenylethylamine
Interesting Amines
Interesting Amines: Alkaloids

nicotine cocaine

morphine

caffeine
Properties & Reactions
Diazotization Reaction

Aryl diazonium salts are

useful synthetic intermediates
(N2 is a good leaving group)
 Azo Dyes

Source: Smith, 2011.

Amino Acids

11
Structures of Amino Acids

12
Isoelectric point

13
Source: Smith, 2011.
Isoelectric point

Source: McMurry, 2012.

14
Standard Amino Acids
O
H2N CH C OH
H

Glycine
Gly, G
15
16
 Essential Amino Acids

Phe Val Thr Trp Ile Met

PVT. TIM HALL

(Private Tim Hall)

His Arg Leu Lys 17

Other Amino Acids

18
Source: McMurry, 2012.
 Structures of Amino Acids

19
Source: McMurry, 2012.
 Electrophoresis of Amino Acids

20
Source: Wade, 2002.
 Chromatography of Amino Acids

21
Source: Wade, 2002.
Peptide Bond

22
Peptide Bond

23
 Ninhydrin Test

(+) towards amino acids, peptides and proteins

24
Source: McMurry, 2012.
 Biuret Test

Cu2+

(+) towards molecules with ≥ 2 peptide bonds

biuret 25
 Peptide Sequencing

Sanger’s Method

Edman Degradation

26
 Peptide Sequencing

1-Fluoro-2,4-DiNitroBenzene – Sanger’s Reagent

27
 Peptide Sequencing

Phenyl isothiocyanate – Edman Reagent*

28
Source: Smith, 2011.
Partial Hydrolysis of Peptides

29
 Partial Hydrolysis of Peptides

Chymotrypsin cleaves here Trypsin cleaves here

N-terminal Ala−Phe−Gly−Leu−Trp−Val−Arg−His−Pro−Pro−Gly
Ala−Phe−Gly−Leu−Trp−Val−Arg−His−Pro−Pro−Gly C-terminal

Carboxypeptidase cleaves here30

Source: Smith, 2011.