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Interpretation:
The explanation of structural features of a linker, which make it possible for the polypeptide to be detached from the Wang resin using trifluoroacetic acid, is to be given.
Concept introduction:
In solid-phase peptide synthesis (SPPS), peptides are prepared, residue by residue. The peptide is attached to
The polypeptide is finally cleaved from the polymer support and is purified by HPLC (high-performance liquid chromatography). The Wang resin is used as polymer support for the batch synthesis of peptide acids following the Fmoc- or tert-Bu-protection. It is cleaved by TFA.
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Chapter 24 Solutions
ORGANIC CHEMISTRY-WILEYPLUS ACCESS PKG.
- On complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one phenylalanine, and one valine residue. Partial hydrolysis gives the following fragments: Ala-Phe, Leu-Met, Val-Ala, Phe-Leu. It is known that the first amino acid in the sequence is valine and the last one is methionine. What is the complete sequence of amino acids?arrow_forward22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forwardGive the sequence of the following tetrapeptide:arrow_forward
- Give the amino acid sequence of each peptide using the fragments obtained by partial hydrolysis of the peptide with acid. a. a tetrapeptide that contains Ala, Gly, His, and Tyr, which is hydrolyzed to the dipeptides His-Tyr, Gly-Ala, and Ala-His b. a pentapeptide that contains Glu, Gly, His, Lys, and Phe, which is hydrolyzed to His-Gly-Glu, Gly-Glu-Phe, and Lys-Hisarrow_forwardAnother method to form a peptide bond involves a two-step process Reaction of the p-nitrophenyl ester with an amino acid ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forwardA tripeptide on hydrolysis produced glycine, alanine and leucine. The structures of these amino acids are shown below. On reaction with Edman’s reagent, leucine was released as the phenylhydantoin. Treatment of the tripeptide with carboxypeptidase gave glycine. Draw the structure of the tripeptide.arrow_forward
- Phenylalanine as N-termminus is incorrect. Please provide the correct solution.arrow_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_forward(a) Draw a structural formula for the products formed when alanine is treated with the following reagents. (i) (Boc)20, NaOH (ii) CbzCI, NazCO3 (iii) 2-Methylpropene, p-TSOH (b) Enfuvirtide, a 36-amino-acid peptide drug, was manufactured at a multi-tonne per year scale. The manufacture relied on solid phase synthesis with Barlos resin as the solid support. Part of the solid phase synthesis is shown below. Write the structure of the product A and discuss the cleavage mechaniśm of the peptide from the resin. 1. Fmoc-Leu-OH, DIPEA 2. 20% piperidine in DMF 3. Fmoc-Glu('Bu)-OH, HBTU, HOBt 4. 20% piperidine in DMF 5. Fmoc-Leu-OH, HBTU, HOBT 6. 20% piperidine in DMF 7. Fmoc-Leu-OH, HBTU, HOBE 8. 20% piperidine in DMF 9. 10% HOAC in CH2CI2 Barlos resinarrow_forward
- Which would you expect to be more soluble in water, a peptide containing mostly alanine and leucine or a peptide containing mostly lysine and aspartic acid? Explain. (Hint: Consider side-chain interactions with water.)arrow_forwardWhat peptides are expected to be produced when a-melanotropin (Problem 2) is cleaved by (a) trypsin, (b) cyanogen bromide, and (c) thermolysin?arrow_forward(please show the proces):The number of peptide bonds in the following structure is:arrow_forward
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