Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 26.15, Problem 22P
Interpretation Introduction
Interpretation:
The steps involved in the synthesis of
Concept Introduction:
Direct reaction between two amino acids results in a mixture of four dipeptides.
Synthesis of a particular dipeptide as the sole product requires protecting the
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Write the complete structures for the following peptides. Tell whether each peptide is acidic, basic, or neutral.(a) methionylthreonine (b) threonylmethionine
Draw the structure of the tetrapeptide Asp-Arg-Val-Tyr. Please show the appropriate stereochemistry of the natural amino acids in the resulting peptide. Please draw all ionizable groups in their neutral form.
A tripeptide undergoes complete hydrolysis and the resulting mixture contains only phenylalanine and glycine. Draw all possible sequences for the original tripeptide.
Chapter 26 Solutions
Organic Chemistry - Standalone book
Ch. 26.1 - Prob. 1PCh. 26.2 - Prob. 2PCh. 26.2 - Prob. 3PCh. 26.3 - Prob. 4PCh. 26.3 - Prob. 5PCh. 26.4 - Prob. 6PCh. 26.4 - Prob. 7PCh. 26.4 - Prob. 8PCh. 26.5 - Prob. 9PCh. 26.6 - Prob. 10P
Ch. 26.6 - Prob. 11PCh. 26.6 - Prob. 12PCh. 26.7 - Prob. 13PCh. 26.7 - Prob. 14PCh. 26.7 - Prob. 15PCh. 26.7 - Prob. 16PCh. 26.7 - Prob. 17PCh. 26.9 - Prob. 18PCh. 26.10 - Digestion of the tetrapeptide of Problem 26.18...Ch. 26.12 - Prob. 20PCh. 26.12 - Prob. 21PCh. 26.15 - Prob. 22PCh. 26.15 - Prob. 23PCh. 26.16 - Prob. 24PCh. 26.17 - Prob. 25PCh. 26.18 - Prob. 26PCh. 26 - Prob. 27PCh. 26 - Prob. 28PCh. 26 - Prob. 29PCh. 26 - Prob. 30PCh. 26 - Prob. 31PCh. 26 - Prob. 32PCh. 26 - Prob. 33PCh. 26 - Prob. 34PCh. 26 - Prob. 35PCh. 26 - Prob. 36PCh. 26 - Prob. 37PCh. 26 - Prob. 38PCh. 26 - Prob. 39PCh. 26 - Prob. 40PCh. 26 - If you synthesized the tripeptide Leu-Phe-Ser from...Ch. 26 - Prob. 42PCh. 26 - Prob. 43PCh. 26 - Prob. 44PCh. 26 - Prob. 45DSPCh. 26 - Prob. 46DSPCh. 26 - Prob. 47DSPCh. 26 - Prob. 48DSPCh. 26 - Prob. 49DSPCh. 26 - Prob. 50DSP
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 22-17 What are the similarities and differences in the structures of alanine and phenylalanine?arrow_forward22-35 Why is histidine considered a basic amino acid when the pKa of its side chain is 6.0?arrow_forward22-71 Which amino acid side chain is most frequently involved in denaturation by reduction?arrow_forward
- 22-29 Draw the structure of a tripeptide made of threomne, arginine, and methionine.arrow_forwarddraw the structures from a trypsin-catalysed reaction of Ala-Lys-Serarrow_forwardWrite out the steps for the synthesis of each peptide using the Merrifield method: (a) Ala–Leu–Phe–Phe; (b) Phe–Gly–Ala–Ile.arrow_forward
- What reaction conditions are needed to achieve complete peptide hydrolysis to its amino acid components? Draw a curly arrow mechanism for hydrolysis of a peptide bond under these conditions.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_forwardDraw the synthesis scheme of the Alanine-Leucine dipeptide. In the synthesis, the tert-butoxycarbonyl protecting groups and the benzyl ester must be used, in addition to the formation of the peptide bond driven by dicyclohexylcarbodiimide.arrow_forward
- In a paragraph form, provide the experimental procedures in the chemical synthesis of protein that contain native serine residues by the reaction of oxazetidine-containing peptides and α-ketoacid.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_forwardPrepare valine from the corresponding: a) aldehyde, b) halocarboxylic acid, c) keto acid, d) nitro acid.arrow_forward
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