Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 29, Problem 29.31P
Devise a synthesis of the following dipeptide from amino acid starting materials.
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Chapter 29 Solutions
Organic Chemistry
Ch. 29 - Prob. 29.1PCh. 29 - Problem 29.2
What form exists at the isoelectric...Ch. 29 - Problem 29.3
Explain why the of the group of an...Ch. 29 - Prob. 29.4PCh. 29 - Problem 29.5
What -halo carbonyl compound is...Ch. 29 - Problem 29.6
The enolate derived from diethyl...Ch. 29 - Problem 29.7
What amino acid is formed when is...Ch. 29 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 29 - Problem 29.9
Draw the products of each...Ch. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Prob. 29.12PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Problem 29.15
Name each peptide using both the...Ch. 29 - Prob. 29.16PCh. 29 - Prob. 29.17PCh. 29 - Problem 29.18
Glutathione, a powerful antioxidant...Ch. 29 - Problem 29.19
Draw the structure of the...Ch. 29 - Problem 29.20
Give the amino acid sequence of an...Ch. 29 - a What products are formed when each peptide is...Ch. 29 - Prob. 29.22PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.25PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.28PCh. 29 - Draw the product formed when the following amino...Ch. 29 - With reference to the following peptide: a...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.32PCh. 29 - Histidine is classified as a basic amino acid...Ch. 29 - Tryptophan is not classified as a basic amino acid...Ch. 29 - What is the structure of each amino acid at its...Ch. 29 - What is the predominant form of each of the...Ch. 29 - 29.37 What is the predominant form of each of the...Ch. 29 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 29 - 29.39 Draw the organic products formed in each...Ch. 29 - 29.40 What alkyl halide is needed to synthesize...Ch. 29 - 29.41 Devise a synthesis of threonine from diethyl...Ch. 29 - 29.42 Devise a synthesis of each amino acid from...Ch. 29 - Prob. 29.43PCh. 29 - Prob. 29.44PCh. 29 - Prob. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.49PCh. 29 - Prob. 29.50PCh. 29 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 29 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 29 - Prob. 29.53PCh. 29 - Prob. 29.54PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.56PCh. 29 - Prob. 29.57PCh. 29 - Prob. 29.58PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - 29.60 Draw the organic products formed in each...Ch. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.63 Besides the Boc and Fmoc protecting groups...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - 29.65 Draw the mechanism for the reaction that...Ch. 29 - 29.66 Which of the following amino acids are...Ch. 29 - 29.67 After the peptide chain of collagen has been...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.71P
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- Write the complete structures for the following peptides. Tell whether each peptide is acidic, basic, or neutral.(a) methionylthreonine (b) threonylmethioninearrow_forwardIdentify an amino acid that complies with the following characteristic: (Write the COMPLETE name) A side chain that reacts with HCl via acid-base reactionarrow_forward22-47 How many different tetrapeptides can be made (a) if the peptides contain the residues of asparagine, proline, serine, and metbionine and (b) if all 20 amino acids can be used?arrow_forward
- 22-42 (a) How many atoms of the peptide bond lie in the same plane? (b) Which atoms are they?arrow_forwardOn 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_forwardGive the complete name of the peptide below.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_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_forwardc) Show the complete reaction if Thyrosine in the aqueous basic solutiond) Draw the dipeptides ofi. Tyr-Metii. Met-Tyrarrow_forward
- Write and name all possible dipeptides from valine and phenylalaninearrow_forwardO alanine glycine Ovaline Oleucine O isoleucine HN Leucine Alanine 1. Excess NH,+ trace acid 3. HC, H₂O + heat Glyche Alm Mis holmainearrow_forward(1) Which is an achiral amino acid? (2) Which is the basic and the acidic amino acid? (3) Which is a a cyclic amino acid?arrow_forward
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