Amino Acids Flashcards
What are amino acids?
- Amino acids are biologically important organic compounds made from amine (-NH2) and carboxylic acid (-COOH) functional groups, along with a side-chain specific to each amino acid.
- The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen, though other elements are found in the side-chains of certain amino acids.
What is the general structure of an amino acid?

How many naturally occuring amino acids are there?
There are 20 naturally occuring amino acids.
What are amino acids used for?
Amino acids function in:
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- Gastrointestinal function
- Cellular energy production
- Detoxification
- Neurotransmitter metabolism
- Muscle catabolism
- Collagen
- Nutritional markers
- Vascular function
What disease processes are amino acid change in sequence implicated in?
Amino acid change in sequence has been implicated in:
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- Cardiovascular disease
- Depression
- Anxiety
- Insomnia
- Chronic Fatigue Syndrome
- Multiple sclerosis
- Congestive heart failure
- Impotence/Erectile pain syndromes
- Infertility
What does chirality mean?
An object or a system is chiral if it is not identical to its mirror image, that is, it cannot be superposed onto it. A chiral object and its mirror image are called enantiomers. A non-chiral object is called achiral and can be superposed on its mirror image.
How would you determine if an amino acid is an L or D isomer?
A rule of thumb for determining the D/L isomeric form of an amino acid is the “CORN” rule. The groups:
<dl>
<dd>
COOH, R, NH2 and H (where R is a variant carbon chain)</dd>
</dl>
are arranged around the chiral center carbon atom. Starting with the hydrogen atom away from the viewer, if these groups are arranged clockwise around the carbon atom, then it is the D-form. If counter-clockwise, it is the L-form.
What is the structure of the amino acid alanine?
- Three letter abreviations: ala
- One letter abreviation: A
- pKa a-carboxyl group, a-ammonium ion and side chain group: 2.34 & 9.69
- Neutral, non-polar

What is the structure of arginine?
- Three letter abreviation: arg
- One letter abreviation: R
- pKa of a-carboxyl group, a-ammonium ion, and side chain group: 2.17, 9.04, and 12.48
- Basic, polar

What is the structure of the amino acid Asparagine?
- Three letter abreviation: asn
- One letter abreviation: N
- pKa a-carboxylic acid & a-amine: 2.02 and 8.80
- Neutral, polar

What is the structure of aspartic acid?
- Three letter abreviation: asp
- One letter abreviation: D
- pKa carboxyl, amino, and R group: 2.10, 9.82, and 3.86
- Acidic, polar

What is the structure of cystine?
- Three letter abreviation: cys
- One letter abreviation: C
- pKa of a-carbon, a-amino, & R group: 2.05, 10.25, & 8.00
- Neutral, slightly polar

What is the structure of glutamic acid?
Three letter abreviation: Glu
One letter abrevation: E
Polar (Charged)

What is the structure of glutamine?
Three letter abreviation: Gln
One letter abreviation: Q
Uncharged, polar

What is the structure of glycine?
Three letter abreviation: Gly
One letter abreviation: G
Nonpolar

What is the structure of histidine?
Three letter abreviation: His
One letter abreviation: H
Polar, + charge

What is the structure of isoleucine?
Three letter abreviation: Ile
One letter abreviation: I
Nonpolar

What is the structure of leucine?
Three letter abreviation: Leu
One letter abreviation: L
Nonpolar

What is the structure of lysine?
Three letter abreviation:
One letter abreviation:
Polar, + charge

What is the structure of methionine?
Three letter abreviation: Met
One letter abreviation: M
Nonpolar, hydrophobic

What is the structure of phenylalanine?
Three letter abreviation: Phe
One letter abreviation: F
Nonpolar

What is the structure of proline?
Three letter abreviation: Pro
One letter abreviation: P
Nonpolar

What is the structure of serine?
Three letter abreviation: Ser
One letter abreviation: S
Polar, uncharged

What is the structure of threonine?
Three letter abreviation: Thr
One letter abreviation: T
Polar, uncharged

What is the structure of tryptophan?
Three letter abreviation: Trp
One letter abreviation: W
Nonpolar

What is the structure of tyrosine?
Three letter abreviation: Tyr
One letter abreviation: Y
Nonpolar

What is the structure of valine?
Three letter abreviation: Val
One letter abreviation: V
Nonpolar

How do the carboxy and amino groups of amino acids exist at physiologic pH?
These groups are ionized at physiologic pH.
What is a Zwitterion?
These are molecules that bear charged grops at opposite polarities (Negative and positive groups).
How many major groups of amino acids are there?
Three: those with nonpolar R groups, those with uncharged polar R groups and those with charged polar R groups.
What are the nine (9) amino acids that have nonpolar R groups?
Glycine
Alanine
Valine
Leucine
Isoleucine
Methionine
Proline
Phenylalanine
Tryptophan
What are the six (6) amino acids with uncharged polar side chains?
Serine
Threonine
Asparagine
Glutamine
Tyrosine
Cysteine
What are the five (5) amino acids that have charged polar R groups?
Lysine
Arginine
Histidine
Aspartic acid
Glutamic acid
What makes cysteine unique among the 20 amino acids?
Cysteine has a thiol group that allows it to form disulfide bonds with another cysteine via an oxidation reaction. The disulfide bond has important implications for protein structure.

What is the isoelectric point (pI) of an amino acid?
This is the point where an amino acid carries no net electric charge.
At a pH below their pI, proteins carry a net positive charge; above their pI they carry a net negative charge.
The pI value can affect the solubility of a molecule at a given pH. Such molecules have minimum solubility in water or salt solutions at the pH that corresponds to their pI and often precipitate out of solution.
Why is the pKa of acetic acid (4.76) higher than that of the amono acid glycine?
NOTE: Acetic acid is an alpha amino derivative of glycine.
This large pKa difference is caused by the electrostatic influence of glycines positively charged ammonium group. That is, the -NH3 + group repels the proton from its COOH group. Conversley, the COOH group increases the basicicity of the amino group.
What is a racemic mixture?
This is a mixture of chiral molecules that has equal amounts of an enantiomeric pair.