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Weston

Holzinger - Understanding Biochemistry


Amino Acid Structure
Constant groups At physiologic blood pH.
O
O ||
|| +H3N
C CO-
H2N C COH

| Hypothetical Organic |
R Chemistry form. R
Amino acids are all composed of three major groups connected to one central __________ carbon.
o The first two groups produce the name:
__________________ (-NH3+)
this functional group has a pKa 9. Therefor it has a ____ charge at blood pH.
_______________________________ (-COO-)
this functional group has a pKa 5. Therefor is has a ____ charge at blood pH.
These groups are called constant because their structure is _______________ across all AA.
o The third is called the R group. This is called the _______________ part of the amino acid.
R groups

-CH2(CH2)12CH3 NH2 NH3+ S-H


PO42

OH COO S-CH3
Hydrophobic Polar Ionic Sulfur Aromatic
R groups make each amino acid unique.
o They can be split into categories based on what they contain atomically.
It can then be assumed that this will affect their _________________.
o A few examples and characteristics of each are below.
Hydrophobic
________________________ (CH3)
Hydrogen
________________________ (H) is the smallest amino acid having only a hydrogen
for an R group. This will be important during discussion of fibrous proteins.
Aromatic
________________________ (CH2-C6H5)
________________________ (CH2-C6H5-CH3)
Polar, uncharged
________________________ (CH2OH)
________________________ (CHCH3OH)
Polar, charged
________________________ (CH2CH2COO-)
________________________ (CH2 CH2 CH2 CH2NH3+)
Sulfer
________________________ (CH2CH2SCH3)
________________________ (CH2-SH)
o This is called a ____________________ group, and is held by this AA alone of
the 20 dominating the human body.
o This will be important in protein tertiary structure.
o Note: You will not need to identify these from memory. It is just wise to know key features.
Amino Acid Structure 1.2.I
Weston Holzinger - Understanding Biochemistry

III O Diprotic Characteristics of Amino Acids


||
H2N C CO- III

pH

|
R
9
O
II
||
+H N C CO- II
3 Isoelectric point (pH)

| Zwitter ion form
R
3
O
I
||
+H N CO-H I
3 C

| Increasing OH-
R

Every amino acid has, for certain, at least _______ acid/base functional groups (H+ donor or acceptor).
o Therefor there are two opportunities for the molecule to act as a ______________.
This is represented by the ___________________ areas of the curve above.
As base is added, the pH should _________________. But at some points this levels off while
changing the charges of the functional groups.

o The pKa for the carboxylic acid group is approximately 3.
As base is added to the system (from a pH of 1 for example) the amino acid will begin to
lose ______________. As the pH of ____ is approached, more and more of form I will be
converted into form II. When there are ____________ amounts of I and II we will have a
perfect buffer solution.
Therefor the curve becomes horizontal at this level.
As the addition of base continues, the buffer becomes less and only form II is present.

o The pKa for the amino group is approximately 9.
Therefore it is at this ______ where the amino group will get to act as a good buffer.
The same circumstances apply as above.

o Zwitter Ion
In form II the amino acid has two charged groups, yet has no ______ charge.
This is referred to as a ______________________.
The level on the pH scale at which this occurs is called the ______________________________.
You can find this point mathematically by taking the _______________ of the pKas.
For example, in this instance we have a pKa of 3 and 9.
o Thus the isoelectric point is _____.

o R groups
It is important to note that the addition of an acid/base functional group can be
achieved if the R group has one. Therefor one more level area would be present.

Diprotic Characteristics of Amino Acids 1.2.I