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Concept explainers
(a)
Interpretation:
The given reaction is to be completed.
Concept Introduction:
Sodium cyanoborohydride is a strong reducing agent. It will reduce the imine formed into the corresponding
(b)
Interpretation:
The given reaction is to be completed.
Concept Introduction:
Acyl nucleophilic substitution reaction takes place at the acyl carbon of the anhydride. The lone pair of the nitrogen atom of amino group of the side chain of lysine acts as nucleophile. The carbonyl carbon of the succinic anhydride acts as the electrophilic centre.
(c)
Interpretation:
The given reaction is to be completed.
Concept Introduction:
The cysteine residue of the amino acid contains side chain
(d)
Interpretation:
The given reaction is to be completed.
Concept Introduction:
The carbonyl carbon of
(e)
Interpretation:
The given reaction is to be completed.
Concept Introduction:
The reaction of amine group with the sodium nitrite results in the formation of dizonium salt. The diazonium salt gives electrophilic
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Chapter 27 Solutions
EBK ORGANIC CHEMISTRY
- Write the complete structures for the following peptides. Tell whether each peptide is acidic, basic, or neutral.(a) methionylthreonine (b) threonylmethionine(c) arginylaspartyllysine (d) Glu-Cys-Glnarrow_forwardWhat is the structure of below amino acid at its isoelectric point: (a) alanine;arrow_forwardExplain why the pI of lysine is the average of the pKa values of its two protonated amino groups.arrow_forward
- If you were to design a small peptide with a large net negative charge at physiological pH, which amino acid residues should predominate?arrow_forward(a) Redraw the tripeptide in zwitterionic form (b) Explain how ESI-MS can be used to determine which amino acid is in the middle of the sequence.arrow_forwardReaction of the a-carboxyl group of an amino acid or peptide with phenylisothiocyanate allows for the determination of the amino acid residue in the N- terminus of an unknown peptide O True O Falsearrow_forward
- indicate the RIGHT alternative: (a) The Zwitterion form of an amino acid exists only at a point pH value. (b) In a peptide bond there is free rotation at the C-N bond. (c) In a polypeptide, the terminal carboxyl group may be present in its amide form. (d) At a pH greater than pI, an amino acid tends to move towards the cathode in an electrophoresis. (e) At any pH below pI, the predominant form of an amino acid is negatively charged.arrow_forwardDraw three-dimensional representations of the following amino acids. Explain their structures. (a) L-phenylalanine (b) L-histidine (c) D-serine (d) L-tryptophanarrow_forwardA normal polypeptide and a mutant of the polypeptide were hydrolyzed by an endopeptidase under the same conditions. The normal and mutant poly peptide differ by one amino acid. The fingerprints of the peptides obtained from the two polypeptides are shown below. What kind of amino acid substitution occurred as a result of the mutation? (That is, is the substituted amino acid more or less polar than the original amino acid? Is its pI lower or higher?)arrow_forward
- Draw zwitterion forms of these amino acids. (a) Valine (b) Phenylalanine (c) Glutaminearrow_forwardDraw out the peptide IYV and clearly label/identify all the Phi, Psi, and peptide bonds present in the peptide. Be sure to draw out the entire peptide and label the N- and C-termini. Which type of secondary structure would this peptide most likely take on (assuming it would take on a secondary structure)?.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_forward
- World of Chemistry, 3rd editionChemistryISBN:9781133109655Author:Steven S. Zumdahl, Susan L. Zumdahl, Donald J. DeCostePublisher:Brooks / Cole / Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
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