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4. The molecular structure of the last 12 amino acid residues (dodecapeptide) that comprise the C- terminal segment of semaglutide is shown below. H3N* NH₂ NH HO 01 NH FO NH CH 3 NH CH3 CH 3 NH ΝΗ ΝΗ CH3 O CH3 O NH H₂C NH CH3 a) Determine the sequence of the dodecapeptide in one-letter code: b) Convert your sequence in (a) into three-letter code: H₂N O NH NH NH H NH H₂N NH 0= NH NH H c) How many of the a-carbons in this peptide sequence are chiral? d) How many peptide bonds are in this peptide? e) Predict the overall charge of this peptide at physiological pH. f) A biochemist synthesized the C-terminal dodecapeptide version of semaglutide but found that there were other contaminating peptides. Based on your answer in (4.e), which ion exchange chromatography technique would you use to effectively purify the dodecapeptide from the mixture? (encircle one) anion exchange cation exchange g) Briefly explain your answer in (4.f).

4. The molecular structure of the last 12 amino acid residues (dodecapeptide) that comprise the C- terminal segment of semaglutide is shown below. H3N* NH₂ NH HO 01 NH FO NH CH 3 NH CH3 CH 3 NH ΝΗ ΝΗ CH3 O CH3 O NH H₂C NH CH3 a) Determine the sequence of the dodecapeptide in one-letter code: b) Convert your sequence in (a) into three-letter code: H₂N O NH NH NH H NH H₂N NH 0= NH NH H c) How many of the a-carbons in this peptide sequence are chiral? d) How many peptide bonds are in this peptide? e) Predict the overall charge of this peptide at physiological pH. f) A biochemist synthesized the C-terminal dodecapeptide version of semaglutide but found that there were other contaminating peptides. Based on your answer in (4.e), which ion exchange chromatography technique would you use to effectively purify the dodecapeptide from the mixture? (encircle one) anion exchange cation exchange g) Briefly explain your answer in (4.f).

Biochemistry
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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**The Molecular Structure of the Last 12 Amino Acid Residues of Semaglutide** The diagram presents the molecular structure of the last 12 amino acid residues (dodecapeptide) forming the C-terminal segment of semaglutide. **Tasks:** a) **Determine the Sequence in One-Letter Code:** - ________________________________________________________ b) **Convert Your Sequence into Three-Letter Code:** - ________________________________________________________ c) **Identify the Chiral α-Carbons:** - How many of the α-carbons in this peptide sequence are chiral? - ________________________________________________________ d) **Count the Peptide Bonds:** - How many peptide bonds are in this peptide? - ________________________________________________________ e) **Predict the Overall Charge at Physiological pH:** - ________________________________________________________ f) **Ion Exchange Chromatography Technique:** - A biochemist synthesized the C-terminal dodecapeptide version of semaglutide but found other contaminating peptides. Based on your charge prediction, which ion exchange chromatography technique would be most effective to purify the dodecapeptide? (Encircle one) - **Anion exchange** - **Cation exchange** g) **Explanation of Chromatography Choice:** - Briefly explain your answer in (f). - ________________________________________________________
Transcribed Image Text:**The Molecular Structure of the Last 12 Amino Acid Residues of Semaglutide** The diagram presents the molecular structure of the last 12 amino acid residues (dodecapeptide) forming the C-terminal segment of semaglutide. **Tasks:** a) **Determine the Sequence in One-Letter Code:** - ________________________________________________________ b) **Convert Your Sequence into Three-Letter Code:** - ________________________________________________________ c) **Identify the Chiral α-Carbons:** - How many of the α-carbons in this peptide sequence are chiral? - ________________________________________________________ d) **Count the Peptide Bonds:** - How many peptide bonds are in this peptide? - ________________________________________________________ e) **Predict the Overall Charge at Physiological pH:** - ________________________________________________________ f) **Ion Exchange Chromatography Technique:** - A biochemist synthesized the C-terminal dodecapeptide version of semaglutide but found other contaminating peptides. Based on your charge prediction, which ion exchange chromatography technique would be most effective to purify the dodecapeptide? (Encircle one) - **Anion exchange** - **Cation exchange** g) **Explanation of Chromatography Choice:** - Briefly explain your answer in (f). - ________________________________________________________
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