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Lewis Dot Structure of ACTH

Posted by Jim Clark on 21st August and posted in Organic Chemistry

This entry is part 1 of 1 in the series High School Chemistry
In this extra credit assignment, you will draw a picture of an important protein. Proteins are important to living organisms:

a. in a structural sense (membranes, connective tissue)
b. for transport mechanisms (hemoglobin)
c. for maintenance of fluid balance (blood serum albumin)
d. for regulation of metabolism (hormones)
e. in genetics (nucleoproteins)
f. in defense mechanisms (blood gamma-globulins)
g. enzymes for catalyzing biologically important chemical reactions.

The particular protein to be constructed on paper will be ACTH, otherwise known as adrenocortico-tropic hormone. Why draw ACTH?

1. ACTH is a relatively small protein with only 39 amino acid groups linked by peptide bonds. It is single chained. Thus it is relatively easy to draw.

2. This assignment is probably a highly stressful one as is your entire experience with high school chemistry. And yet, ACTH is a pituitary hormone which the body releases exactly in response to the environmental stress that this assignment is designed to produce. Thus, while you are constructing external models of ACTH, you will likely be experiencing internal feelings that stem directly from your own secretion of this corticosteroid. You will also secrete ACTH in response to other, less disagreeable problems such as infectious diseases and traumatic shock, to name but two.

The amino acid sequence in ACTH is:
Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-
Gly-Lys-Lys-Arg-Arg-Pro-Val-Lys-Val-Tyr-Pro-Ala-Gly-
Glu-Asp-Asp-Glu-Ala-Ser-Glu-Ala-Phe-Pro-Leu-Glu-Phe

In order to draw this, you will need to know:
1. the structural formulas of the amino acids
2. how to connect amino acids by way of peptide bonds (See the same reference)
You should use modified Lewis dot structures such that bonds are represented by lines (each line is a pair of electrons shared by the two atoms). Non-bonding electron pairs are shown as dots. Thus molecular oxygen would be drawn as:

The amino acid, tyrosine, which appears in the chart as:

Should be written

Note that whenever a ring is drawn, the short hand notation used omits all hydrogens attached to ring carbons. You must supply them to give each carbon its four bonds. To give you a head start, here are the first four amino acids:

wpe2.gif (8187 bytes)

or

wpe3.gif (10172 bytes)

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