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Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Textbook Question
Chapter 29, Problem 29.44P
Devise a synthesis of each amino acid from acetaldehyde (
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2.
Classify the following amino acids as nonpolar, polar basic, polar acidic, or polar neutral.
(a)
(b)
(c)
(d)
H₂N-CH-COH
CH-OH
I
CH3
||
H₂N-CH-C-OH
I
CH₂
C=O
1
OH
H₂N-CH-C-OH
CH₂
T
CH-CH3
CH₂
H₂N-CH-C-OH
ī
CH₂
OH
229
5
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 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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- Draw the product formed when the following amino acid is treated with each reagent: (a) CH3OH, H+; (b) CH3COCl, pyridine; (c) HCl (1 equiv); (d) NaOH (1 equiv); (e) C6H5N=C=S.arrow_forwardwrite the IUPAC names for the following aminos CH,CH, CH;CH,NH2 b) CH;CH, c) CH 9. Escriha la aetunt -.arrow_forwardDraw both enantiomers of each amino acid and label them as R or S: (a) phenylalanine; (b) methionine.arrow_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_forwardDraw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin, appeared in Section 22.6B.)arrow_forward(a) Provide four distinct forms of phenylalanine. (b) Rank the solubility of these forms in water. (c) Explain your ranking.arrow_forward
- Alanine is one of the 20 amino acids (it contains both an amino and a carboxyl group) found in proteins - \, Is alanine better represented by structural formula A or B? Explain. CH-CH-Ö-OH CH-CH-Ö-o- NH, NH3" (A) (B)arrow_forwardTreating chitin with H2O, -OH hydrolyzes its amide linkages, forming a compound called chitosan. What is the structure of chitosan? Chitosan has been used in shampoos, bers for sutures, and wound dressings.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
- Draw the structure of the predominant form of a mixture of alanine, lysine, and aspartic acid at (i) pH 6; (ii) pH 11; (iii) pH 2.arrow_forward3. Classify the following as a lipid, carbohydrate, or amino acid: (EOCQ 58) CH,OC(CH,)12CH, CHOC(CH,),,CH, CH,0C(CH,),CH=CH(CH,),CH, a.arrow_forwardA chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forward
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