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QUESTION

It is your first week in the lab and you are given the task of modifying insulin to make it more hydrophobic by modifying one or more of its amino...

It is your first week in the lab and you are given the task of modifying insulin to make it more hydrophobic by modifying one or more of its amino acids. You notice there are several serine amino acids in the structure of insulin.

A.    Identify all the organic functional groups in a molecule of serine. Identify the atom(s) in serine that may be chiral? How can you tell if the atom is chiral?

B.    You would like to convert serine into an ester, but still allow it to form peptide bonds within the insulin structure. Draw the reaction of serine with acetic acid to form an ester. Why would converting all the serine amino acids into esters make insulin more hydrophobic?

C.    Hydrochloric acid is used to catalyze the reaction to convert serine into an ester. For your experiment you need to prepare 100 mL of an aqueous 0.10 M solution of HCl. You have a bottle of hydrochloric acid that is 36% m/m in concentration (36 g HCl per 100 g of aqueous solution). The density of 36% HCl is 1.18 g/mL at the temperature you are preparing. Show your calculations and list the steps you would take to prepare 100 mL this solution from 36% m/m HCl.

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