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    Session #31: Homework Solution: Problem #1

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    Pradipta B
    The document summarizes solutions to 6 problems about amino acids and their properties. Problem 1 ranks amino acids by their migration in electrophoresis at pH 7.3. Problem 2 defines isoelectric point (pI) and gives examples for alanine and lysine. Problem 3 describes which amino acids migrate toward the cathode or anode in a mixture at pH 7.1. Problem 4 and 5 show structures of dipeptides and tetrapeptides at pH 7. Problem 6 calculates the pI of cysteine using its pKa values.

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    Session #31: Homework Solution: Problem #1

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    Pradipta B
    48 views5 pages
    The document summarizes solutions to 6 problems about amino acids and their properties. Problem 1 ranks amino acids by their migration in electrophoresis at pH 7.3. Problem 2 defines isoelectric point (pI) and gives examples for alanine and lysine. Problem 3 describes which amino acids migrate toward the cathode or anode in a mixture at pH 7.1. Problem 4 and 5 show structures of dipeptides and tetrapeptides at pH 7. Problem 6 calculates the pI of cysteine using its pKa values.

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    The document summarizes solutions to 6 problems about amino acids and their properties. Problem 1 ranks amino acids by their migration in electrophoresis at pH 7.3. Problem 2 defines isoelectric point (pI) and gives examples for alanine and lysine. Problem 3 describes which amino acids migrate toward the cathode or anode in a mixture at pH 7.1. Problem 4 and 5 show structures of dipeptides and tetrapeptides at pH 7. Problem 6 calculates the pI of cysteine using its pKa values.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    48 views5 pages

    Session #31: Homework Solution: Problem #1

    Uploaded by

    Pradipta B
    The document summarizes solutions to 6 problems about amino acids and their properties. Problem 1 ranks amino acids by their migration in electrophoresis at pH 7.3. Problem 2 defines isoelectric point (pI) and gives examples for alanine and lysine. Problem 3 describes which amino acids migrate toward the cathode or anode in a mixture at pH 7.1. Problem 4 and 5 show structures of dipeptides and tetrapeptides at pH 7. Problem 6 calculates the pI of cysteine using its pKa values.

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    Session #31: Homework Solution

    Problem #1

    Rank the following amino acids in decreasing order of migration towards the
    cathode (negative electrode) when separated by electrophoresis in a solution of
    pH = 7.3.

    I. Lysine: pI = 9.87
    II. Alanine: pI = 6.02
    III. Aspartate: pI = 5.95

    Solution

    I > II > III

    Problem #2

    Define what is meant by isoelectric point (pI) and give an example.

    Solution

    Isoelectric point is the pH of an amino acid at which it has no net electric charge. For
    amino acids that have no ionizable side chain, the pI value is the average of its two pKa’s.
    If the amino acid has an ionizable side chain, the pI value is the average of the pKa’s of
    similarly ionizable groups.

    Ex:

    Alanine:

    pK a = 9.69

    2.34 + 9.69
    pI= = 6.02
    2

    Ex.

    Lysine:
    Lysine:

    10.79 + 8.95
    pI = = 9.87
    2

    Problem #3

    You are given a mixture that contains glutamic acid (pI = 3.2), arginine (pI = 10.8),
    and valine (pI = 6.0), and you subject the mixture to electrophoresis.

    (a) Which amino acids migrate towards the cathode when the electrophoresis is
    carried out at a pH of 7.1?

    (b) Which amino acids migrate toward the anode when the electrophoresis is
    carried out at a pH of 7.1?

    (c) Which amino acid migrates farthest toward the anode at a pH of 7.1?

    Solution

    a) arginine
    b) valine and glutamic acid
    c) glutamic acid

    Problem #4

    Draw the dipeptide Val-Tyr at pH 7.0.

    Solution
    Problem #5

    Draw the structure of the tetrapeptide Ser-Leu-Phe-Pro at pH 7.0.

    Solution

    Problem #6

    The pKa values for the α-carboxylic acid and the α-amino acid groups is cysteine are
    1.092 and 10.78, respectively. The pKa for the titratable −SH side chain in the
    amino acid is 8.33. Calculate the pI of cysteine.

    Solution

    The structure of cysteine at pH = 7 shows that the side group is protonated. So we must
    conclude that even though the pKa is 8.33, the sulfhydryl (−SH) is acting as an acid.

    The isoelectric point, pI, is the pH at which the zwitterion is the dominant species.

    Let’s start with extreme acid conditions, pH < 1.96. Under these circumstances according
    to the LeChatelier Principle the amino acid will be fully protonated in an effort to try to
    consumer the proton excess in solution. The resulting structure of the amino acid is

    , which is net positive (cationic).

    In slightly more alkaline solutions, 1.96 < pH < 8.33, the carboxylic acid sheds its proton in
    order to neutralize OH-. The resulting structure of the amino acid is
    , which is the zwitterion. Hence we calculate the value of pI to be the average of 1.06
    and 8.33 = 5.14.

    Just to complete the analysis, consider still greater basicity, 8.33 < pH < 10.78. Over
    this range of composition the resulting structure of the amino acid is

    , which is net negative (anionic).

    Finally, at extreme alkaline conditions, pH > 10.78, everything is deprotonated in an effort to


    neutralize the rising OH- population. Over this range of composition the resulting structure of
    the amino acid is

    , which is net negative and doubly charged (anionic).


    Also worth mentioning, at neutral pH, reduced sulfhydryls on two different cysteine side
    groups can be oxidized to form disulfide linkages.
    MIT OpenCourseWare
    http://ocw.mit.edu

    3.091SC Introduction to Solid State Chemistry


    Fall 2009

    For information about citing these materials or our Terms of Use, visit: http://ocw.mit.edu/terms.

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