Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 29, Problem 29.19P
Draw the structure of the
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With reference to the following peptide: (a) Identify the N-terminal and Cterminal amino acids. (b) Name the peptide using one-letter abbreviations. (c) Label all the amide bonds in the peptide backbone.
(a) Draw the structure of the two possible dipeptides that can be formed by combining valine and phenylalanine. (b) In each dipeptide, label the N- and C-terminal amino acids. (c) Name each peptide using three-letter symbols.
Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu.
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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- (A) How many peptide bonds are present in peptide 1? (B) What is the N-terminal amino acid in peptide 2? (C) What is the C-terminal amino acid in peptide 2?arrow_forward2. What is the oral absorption of a drug? Describe completely. 3. What is the following structure about? Describe with details. PEPTIDE(1) PEPTIDE(1) NH NH NH- ---HN SERINE PROTEASE H 0 0 E CO₂H CO---- 0= HN- in the CO₂H CO₂H PENICILLINS -HN SERINE PROTEASEarrow_forward3. What is the product if the following peptide is hydrolyzed? H₂N O OHarrow_forward
- Which of the following amous indicates the peptide bond? CA) (B) (C) (D) (E) fut H₂N-CH-C-N-CH-C-OH CHPH H CH3arrow_forwardThe following compound is an intermediate in the biosynthesis of one of the 20 common -amino acids. Which one is it likely to be, and what kind of chemical change must take place to complete the biosynthesis?arrow_forwardFor the tripeptide SerValMet a. What amino acid is located at the peptides N-terminal end? b. What amino acid is located at the peptides C-terminal end? c. How many peptide bonds are present? d. How many amide linkages are present?arrow_forward
- Following is the primary structure of glucagon, a polypeptide hormone of 29 amino acids. Glucagon is produced in the -cells of the pancreas and helps maintain blood glucose levels in a normal concentration range. Which peptide bonds are hydrolyzed when this polypeptide is treated with each reagent? (a) Phenyl isothiocyanate (b) Chymotrypsin (c) Trypsin (d) BrCNarrow_forwardAnswer the following questions about the amino acid whose Fischer projection formula is a. Is it a D-amino acid or an L-amino acid? b. Is it a nonpolar or polar amino acid? c. Is it an essential or nonessential amino acid? d. Is it a standard or nonstandard amino acid?arrow_forward22-25 Draw the most predominant form of lysine at its isoelectric point.arrow_forward
- How prepare g-C3N4 from urea in laboratory?arrow_forward3. Pepsin cleavage of the peptide Ala-His-Gly-Trp-Val-lle-Arg-Gly would yield the peptides Ala-His-Gly-Trp and Val-Ile-Arg-Gly. 4. Argininosuccinate synthetase converts citrulline and aspartate into argininosuccinate. T F T Farrow_forwardBacteria that live in the large intestine metabolize glycocholic acid using amidases and hydroxylases. (a) Draw the reaction product. (b) Compare the solubility of the product and glycocholic acid. (c) Could the change in the bile acid’s solubility make it less toxic to bacteria?arrow_forward
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