Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 29, Problem 29.58P
Draw the amino acids and peptide fragments formed when the decapeptide A–P–F–L–K–W–S–G–R–G is treated with each reagent or enzyme: (a) chymotrypsin; (b) trypsin; (c) carboxy peptidase; (d)
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Draw the amino acids and peptide fragments formed when the decapeptide A–P–F–L–K–W–S–G–R–G is treated with each reagent or enzyme: (a) chymotrypsin; 8 pt helvetica roman (b) trypsin; (c) carboxypeptidase; (d) C6H5N = C = S.
(a) What is the difference between the hormones progesterone and testosterone?
(b) Draw the structure of a a steroid nucleus.
(c) Give the products obtained from complete base hydrolysis in the following reaction:
O
||
CH,−O−C−(CH2)14–CH3
O
CH–0–C−(CH2)14—CH3 + 3 NaOH
O
CH,−0–C−(CH2)14–CH3
Give the amino acid sequence of a hexapeptide that contains the amino acids Ala, Val, Ser, Ile, Gly, Tyr, and forms the following fragments when partially hydrolyzed with HCl: Gly–Ile–Val, Ala–Ser–Gly, and Tyr–Ala.
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 - 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 - Prob. 29.8PCh. 29 - Prob. 29.9PCh. 29 - Prob. 29.10P
Ch. 29 - Prob. 29.11PCh. 29 - Problem 29.13
What alkene is needed to synthesize...Ch. 29 - Problem 29.14
Draw the structure of each peptide....Ch. 29 - Name each peptide using both the one-letter and...Ch. 29 - Prob. 29.15PCh. 29 - Prob. 29.16PCh. 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. 29.21PCh. 29 - Devise a synthesis of each peptide from amino acid...Ch. 29 - Devise a synthesis of the following dipeptide from...Ch. 29 - Prob. 29.24PCh. 29 - Consider two molecules of a tetrapeptide composed...Ch. 29 - What types of stabilizing interactions exist...Ch. 29 - Prob. 29.27PCh. 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. 29.31PCh. 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 - To calculate the isoelectric point of amino acids...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 - Draw the organic product formed when the amino...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. 29.45PCh. 29 - Prob. 29.46PCh. 29 - Prob. 29.47PCh. 29 - Prob. 29.48PCh. 29 - Prob. 29.49PCh. 29 - 29.48 Brucine is a poisonous alkaloid obtained...Ch. 29 - Prob. 29.51PCh. 29 - Prob. 29.52PCh. 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. 29.55PCh. 29 - Explain why a peptide CN bond is stronger than an...Ch. 29 - Prob. 29.57PCh. 29 - 29.55 Draw the amino acids and peptide fragments...Ch. 29 - Prob. 29.59PCh. 29 - Prob. 29.60PCh. 29 - Prob. 29.61PCh. 29 - 29.59 An octapeptide contains the following amino...Ch. 29 - Prob. 29.63PCh. 29 - Prob. 29.64PCh. 29 - Draw all the steps in the synthesis of each...Ch. 29 - 29.62 Write out the steps for the synthesis of...Ch. 29 - 29.64 Another method to form a peptide bond...Ch. 29 - Prob. 29.68PCh. 29 - Prob. 29.69PCh. 29 - Which of the following amino acids are typically...Ch. 29 - After the peptide chain of collagen has been...Ch. 29 - Prob. 29.72PCh. 29 - Prob. 29.73PCh. 29 - 29.70 The anti-obesity drug orlistat works by...Ch. 29 - Prob. 29.75P
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- 22-48 How many amino acid residues in the A chain of insulin are the same in insulin from humans, cattle (bovine), hogs, and sheep?arrow_forward22-97 Gelatin is derived from collagen by denaturation. Is a gelatin dessert likely to be a good source of dietary protein?arrow_forwardFor the tripeptide GlyAlaCys 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
- 22-104 Why is collagen not a very good source of dietary protein?arrow_forwardConsider the tripeptide leucylvalyltryptophan. a. Specify its structure using three-letter symbols for the amino acids. b. How many peptide bonds are present within the peptide? c. Which of the amino acid residues has the largest R group? d. Which of the amino acid residues, if any, has a basic side chain?arrow_forward22-44 How can a protein act as a buffer?arrow_forward
- Consider the tripeptide tyrosylleucylisoleucine. a. Specify its structure using three-letter symbols for the amino acids. b. How many peptide bonds are present within the peptide? c. Which of the amino acid residues has the largest R group? d. Which of the amino acid residues, if any, has an acidic side chain?arrow_forward22-91 Which amino acid does not rotate the plane of polarized light?arrow_forward14. (a) Identify the acetal and the ketal group in the following disaccharide. (b) Decide whether the compound is a non-reducing or reducing sugar. OH НО HƠ HO Н HO Н НО HO 15. (a) Identify the glycosidic bond in the following disaccharide. (b) Decide whether the compound is a non-reducing or reducing sugar. (c) Polysaccharide units are usually bonded together with a or B 1, 6 or 1, 4 linkages. What linkage is used in the disaccharide shown below? s) НО НО НО HO НО -OH OH -H OH CH2OH 16. Draw the structure for 1,4-B-D-galactopyranosyl-D-glucose. ( но- 17. Assign an R/S designation to each chirality center in the following compound: ( CHO НО -OHarrow_forward
- 4arrow_forward(a) What amino acids would be obtained by hydrolysis of the following tripeptide? H,NCHCNHCHCNHCHCOH (CH)2CH H.CоН Н-ССH-СОН (b) How many different tripeptides can be made from gly- cine, serine, and glutamic acid? Give the abbreviation for each of these tripeptides, using the three-letter codes and one-letter codes for the amino acids.arrow_forwardThe structure of the artificial sweetener aspartame is shown below. What type of linkage is found in this compound? H. +H,N-CH-C-N-CH C-OCH, CH2 CH2 C3D0 Aspartame (Asp-Phe-OMe) O peptide bond O phosphoester linkage O ester linkage O glycosidic linkagearrow_forward
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