Concept explainers
(a)
Interpretation:
The peptides obtained from the cleavage of given peptide chain by trypsin has to be given.
Concept introduction:
Amino acids are linked each other by peptide bonds is called protein (one or more peptide bonds). Peptide bonds are amide bonds, in which carbonyl group of one amino acid bonded to amino group of other amino acid. The chain of the protein is drawn in such a way that left end is occupied by free amino group (say N-terminal) and right side of the chain is occupied by carbonyl group (say C-terminal).
Endopeptidases cleave peptide bonds that are not at the end.
Trypsin is an endopeptidase, which cleave the C-side peptide bond of positively charged side chains such as arginine and lysine.
(b)
Interpretation:
The peptides obtained from the cleavage of given peptide chain by chymotrypsin has to be given.
Concept introduction:
Amino acids are linked each other by peptide bonds is called protein (one or more peptide bonds). Peptide bonds are amide bonds, in which carbonyl group of one amino acid bonded to amino group of other amino acid. The chain of the protein is drawn in such a way that left end is occupied by free amino group (say N-terminal) and right side of the chain is occupied by carbonyl group (say C-terminal).
Endopeptidases cleave peptide bonds that are not at the end.
Chymotrypsin is an endopeptidase, which cleave the C-side peptide bond of amino acids that contain
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Check out a sample textbook solutionChapter 17 Solutions
Essential Organic Chemistry, Global Edition
- A decapeptide has the following amino acid composition. Ala2, Arg, Cys, Glu, Gly, Leu, Lys, Phe, Val Partial hydrolysis yields the following tripeptides. Cys-Glu-Leu + Gly-Arg-Cys + Leu-Ala-Ala + Lys-Val-Phe + Val-Phe-Gly One round of Edman degradation yields a lysine phenylthiohydantoin. From this information, deduce the primary structure of this decapeptide.arrow_forwardAnother method to form a peptide bond involves a two-step process Conversion of a Boc-protected amino acid to a p-nitrophenyl ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forwardAfter the polypeptide shown below was treated with maleic anhydride, it was hydrolyzed by trypsin. (After a polypeptide is treated with maleic anhydride, trypsin will cleave the polypeptide only on the C-side of arginine.) Gly-Ala-Asp-Ala-Leu-Pro-Gly-Ile-Leu-Val-Arg-Asp-Val-Gly-Lys-Val-Glu-Val-Phe-Glu-Ala-GlyArg-Ala-Glu-Phe-Lys-Glu-Pro-Arg-Leu-Val-Met-Lys-Val-Glu-Gly-Arg-Pro-Val-Gly-Ala-Gly-Leu-Trp a. After a polypeptide is treated with maleic anhydride, why does trypsin no longer cleave it on the C-side of lysine? b. How many fragments are obtained from the polypeptide? c. In what order will the fragments be eluted from an anion-exchange column using a buffer of pH = 5?arrow_forward
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- After the polypeptide shown below was treated with maleic anhydride, it was hydrolyzed by trypsin. (After a polypeptide is treated with maleic anhydride, trypsin will cleave the polypeptide only on the C-side of arginine.) Gly-Ala-Asp-Ala-Leu-Pro-Gly-Ile-Leu-Val-Arg-Asp-Val-Gly-Lys-Val-Glu-Val-Phe-Glu-Ala-Gly-Arg-Ala-Glu-Phe-Lys-Glu-Pro-Arg-Leu-Val-Met-Lys-Val-Glu-Gly-Arg-Pro-Val-Gly-Ala-Gly-Leu-Trp How many fragments are obtained from the polypeptide?arrow_forwardPredict the products P and Q formed when the following peptide is treated with the given reagient. HS. H₂N (b) (c) (d) HS P P OH H₂N. PhNCS DIPEA H₂N. X DH P + Q OH CHarrow_forwardWhich of the following reagents can be used to cleave a tert-butoxycarbonyl (Boc) protecting group from a peptide? H₂/Pd CF3CO₂H Na₂CO3, H₂O LiAlH4 Barrow_forward
- Three peptides were obtained from a trypsin digestion of two different polypeptides. In each case, indicate the possible sequences from the given data and tell what further experiment should be carried out in order to determine the primary structure of the polypeptide. a. polypeptide I: 1. Val-Gly-Asp-Lys 2. Leu-Glu-Pro-Ala-Arg 3. Ala-Leu-Gly-Asp b. polypeptide II: 1. Val-Leu-Gly-Glu 2. Ala-Glu-Pro-Arg 3. Ala-Met-Gly-Lysarrow_forwardIn a paragraph form provide the experimental procedure of the reaction of oxazetidine-containing peptides and α-ketoacid that will result in protein that contain native serine residuesarrow_forwardThree peptides were obtained from a trypsin digestion of two different polypeptides. indicate the possible sequences from the given data and tell what further experiment should be carried out in order to determine the primary structure of the polypeptide. polypeptide I: 1. Val-Gly-Asp-Lys 2. Leu-Glu-Pro-Ala-Arg 3. Ala-Leu-Gly-Asparrow_forward
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