ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 24, Problem 14PP
Practice Problem 24.14
The terminal carboxyl groups of glutamic acid and aspartic acid are often protected through their conversion to benzyl esters. What mild method could be used for removal of this protecting group?
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why are peptide amide bonds exist either as s-cis or s-trans conformation?
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The dynorphins are a group of opioid peptides that play an importantrole in changes in the brain associated with cocaine addiction. One ofthese peptides, dynorphin A, contains the following amino acidsequence: Tyr–Gly–Gly–Phe–Leu–Arg–Arg–Ile–Arg–Pro–Lys–Leu–Lys.Draw the amino acids and peptide fragments formed when dynorphin A is treated with each reagent or enzyme: (a) chymotrypsin; (b) trypsin; (c)carboxypeptidase; (d) C6H5N=C=S.
Chapter 24 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 24 - Prob. 1PPCh. 24 - Practice Problem 24.2 The guanidino group NHNHCNH2...Ch. 24 - Prob. 3PPCh. 24 - Prob. 4PPCh. 24 - Prob. 5PPCh. 24 - Prob. 6PPCh. 24 - Prob. 7PPCh. 24 - Practice Problem 24.8
Glutathione is a tripeptide...Ch. 24 - Prob. 9PPCh. 24 - Prob. 10PP
Ch. 24 - Prob. 11PPCh. 24 - Practice Problem 24.12 Show all steps in the...Ch. 24 - Practice Problem 24.13 The synthesis of a...Ch. 24 - Practice Problem 24.14
The terminal carboxyl...Ch. 24 - Prob. 15PPCh. 24 - Prob. 16PPCh. 24 - (a) Which amino acids in Table 24.1 have more than...Ch. 24 - Prob. 18PCh. 24 - 24.19 (a) On the basis of the following sequence...Ch. 24 - Prob. 20PCh. 24 - Prob. 21PCh. 24 - Prob. 22PCh. 24 - Prob. 23PCh. 24 - Prob. 24PCh. 24 - The enzyme lysozyme and its mechanism are...Ch. 24 - Prob. 2LGP
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- Draw a structural formula for the product formed when alanine is treated with the following reagents. (a) Product from (c), L-Alanine ethyl ester, DCC (b) Product from (d), L-Alanine ethyl ester, DCCarrow_forwardAn octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glu (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile–Leu in addition to other products. Deduce the structure of the octapeptide and fragments A–D.arrow_forwardShow how to convert the side-chain carboxyl group to a benzyl ester using benzyl chloride as a source of the benzyl group.arrow_forward
- Subject-advance chemistryarrow_forwardIndicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.arrow_forwardalanine is dissolved in a solution with a pH of 4.2. what percent of the alanine's carboxyl groups are de - protonated at this pH? What percent of the carboxyl groups are protonated?arrow_forward
- A 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_forwardonly question (b)arrow_forwardProline is the only naturally occurring amino acids that can exist in two conformational states referred to as cis and trans proline when incorporated into peptides. a) Draw the cis and trans conformations of the proline containing tripeptide NH(Fmoc)-Val-Pro- Trp-COОH b) In most cases the trans proline amid conformation is preferred. Design two proline mimetics that allow to populate preferably the cis amide rotamer conformation of proline in tripeptide NH(Fmoc)-Val-Pro-Trp-COOH c) Outline strategies that can be used to populate the cis amide state of other amino acids. Use the amino acid ornithine as an examplearrow_forward
- Give a clear handwritten answer with explanation..arrow_forwardGive the amino acid sequence of an octapeptide that contains the amino acids Tyr, Ala, Leu (2 equiv), Cys, Gly, Glu, and Val, and forms the following fragments when partially hydrolyzed with HCl: Val–Cys–Gly–Glu, Ala–Leu–Tyr, and Tyr–Leu–Val–Cys.arrow_forwardDraw the zwitterionic structure of glutamic acidarrow_forward
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