What is the absolute configuration of

most amino acids in nature?

L-Amino Acids
What absolute configuration is found
in proteins?
L-Amino Acids
Essential Amino Acid
Amino acids that must be obtained from
the diet because the body cannot
produce them
What are the Essential Amino Acids?
Methionine, Threonine, Histidine, Valine,
Phenylalanine, Isoleucine, Tryptophan,
Lysine, Leucine
How are amino acids synthesized?
Gabriel Synthesis and Strecker
Synthesis
Gabriel Synthesis
Chemical reaction that transforms
primary alkyl halides into primary
amines
What are the general steps in a
Gabriel Synthesis?
 A primary alkyl halide reacts with
phthalimide forming an alkyl
phthalimide, then phthalimide is cleaved
with hydrazine
Gabriel Synthesis Reaction
 O

N- K+
Strecker SynthesisO
O NH2NH2
R N
R Cl R NH2

O
Chemical reaction that transforms an
aldehyde to an amino acid
What are the general steps in a
Strecker Synthesis?
 Aldehyde reacts with ammonium
chloride and cyanide to create an
α-aminonitrle, then is hydrolyzed in
acidic conditions
Strecker Synthesis Reaction
 NH3 H NH3 H
O H 2N H2N
HCN HCN
C C O
C R a C R a C
R H N
OH
Primary Protein Structure
A sequence of amino acids in a
polypeptide chain
Secondary Protein Structure
Motifs (α-helices, β-sheets, β-turns)
within a polypeptide that form due to
interactions between atoms and the
backbone
Tertiary Protein Structure
The overall three-dimensional structure
of a polypeptide that is formed by the
interactions of the different R groups
Quaternary Protein Structure
Multiple polypeptide chains (subunits) in
a protein complex
α Helix
The carbonyl (C=O) of one amino acid is
hydrogen bonded to the amino H (N-H)
of an amino acid that is four down the
chain, pulling the chain into a helical
structure
Where are the backbones and R
groups in an α Helix?
Backbone line the center of the α Helix
and the R groups are sticking out
β Sheet
Two or more segments of a polypeptide
chain line up next to each other, forming
a sheet-like structure held together by
hydrogen bonds
Parallel β Sheet
 O O O
H H
H 2N N N
N N OH
H H
O O
O O O

H H
H2N N N
N N OH
H H
O O
A
ntiparallel β Sheet
 O O O

H H
H2N N N
N N OH
H H

O O O O O

H H
H 2N N N OH
N N N
H H H

O O O

Which amino acids are considered a

helix breaker?
Proline
What type of motifs are Prolines
typically found in?
β Sheet
Which amino acids are typically
found in β Sheets?
Tryptophan, Tyrosine, Phenylalanine