Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 29, Problem 29.64P
Another method to form a peptide bond involves a two-step process:
[1] Conversion of a Boc-protected amino acid to a p-nitrophenyl ester.
[2] Reaction of the p-nitrophenyl ester with an amino acid ester.
![Chapter 29, Problem 29.64P, 29.64 Another method to form a peptide bond involves a two-step process:
[1] Conversion of a , example 1](http://dev-ingestion-image-output.s3-website-us-east-1.amazonaws.com/9780078021558/Chapter-29/images/21558-29-29.64p-question-digital_image001.jpg)
a. Why does a p-nitrophenyl ester “activate” the carboxy group of the first amino acid to amide formation?
b. Would a p-methoxy phenyl ester perform the same function? Why or why not?
![Chapter 29, Problem 29.64P, 29.64 Another method to form a peptide bond involves a two-step process:
[1] Conversion of a , example 2](http://dev-ingestion-image-output.s3-website-us-east-1.amazonaws.com/9780078021558/Chapter-29/images/21558-29-29.64p-question-digital_image002.jpg)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
1. Biogenic Amines are inactivated primarily by
a. Sulfonation
b. Glucoronidation
c. Aromatic hydroxylation
d. Methylation
2. A drug can exert its pharmacological effect only if it is
a. Protein bound
b. Protein unbound
c. Free drug
d. Both B & C
e. Both A & C
3. In order for the drug to be ready and available for absorption, it must be release first from its dosage form with the exception of:
a. Capsule
b. Tablet
c. Solution
d. Suspension
4. All of the following are true, except
a. Solubility increase with decrease particle size
b. Solubility increase with increase surface area
c. Solubility increase with increase particle size
d. Solubility decrease with decrease surface area
5. The rate in which the drug appears in the bloodstream is also known as
a. Half-life
b. Potency
c. Bioavailability
d. Area under the curve
13. Explain why the dansyl chloride treatment of a single polypeptide chain followed by its complete acid hydrolysis
yields several dansylated amino acids.
9. How do you know if a malenimide based reagent will conjugate to nitrogen or sulphur in an amino acid?
но
protein
-protein
SH
NH2
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
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Ceramide can then be used to synthesize sphingomyelin, another important molecule that is prevalent in cell membranes. 1.How does the structure of sphingomyelin differ from that of ceramide? 2.Sphingomyelin is also found in the cell membrane. Explain how you would expect to find the orientation of this molecule in the cell membrane. 3.Which amino alcohol is used in the synthesis of sphingomyelin? 4.What is particular about the amino alcohol used in in the synthesis of sphingomyelin? 5.How does your answer to #16 affect the physical properties of properties of sphingomyelin?arrow_forward1. Write the synthesis of phenobarbital, give names to the initial and intermediate substances. 2. Name the given substance. What pharmacological group does it belong to? CH3 . H2SO4 . H20 CH2OH 3. Write the metabolism of chlordiazepoxide, name all metabolites. 4. Write the structure of benzocaine, show the fragment of primary aromatic amino group in the structure, write the reaction for it, state the observation. 5. Write the equation for assay of acetylsalicylic acid. Give the value of stoichiometric coefficient, formulas for the calculation of titre and percentage..arrow_forwardNeed help with this question. Thank you :)arrow_forward
- 13. What is the product of the following amidation reaction? transferase -NH2 product ОН yon Н + H20 d. HO- a. `NH2 e. b. H2N ОН + H20 Н C. + H20 N. Нarrow_forwardTo synthesize Tylenol, p-aminophenol will be acetylated using 1.4 equivalents of acetic anhydride. Starting with 2.1 g p-aminophenol, how what volume (in mL) of acetic anhydride is required?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
- What special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forward1. Draw deoxythymidylate (deoxythymidine 5'- monophosphate, dTMP) and glutamic acid. describe summaryarrow_forward15. The quantitative determination of glutamic acid can be carried out: A) Kjeldahl method B) Alkalimetrically (one carboxyl group) B) Alkalimetrically (for two carboxyl groups, linking the amino group with a formaldehyde solution) D) Argentometricallyarrow_forward
- In greater details, what main difference would you see when conducting the nitrous acid test with aniline vs. amino-cyclohexane? Be specific.arrow_forwardShow the detailed experimental procedures for the chemical synthesis of proteins with the α-ketoacid–hydroxylamine (KAHA ligation), using (S)-5-oxaproline (Opr) as a key building block.arrow_forwardDraw the product that valine forms when it reacts with di-tert-butyl dicarbonate and triethylamine followed by an aqueous acid wash. O • You do not have to consider stereochemistry. • Do not draw organic or inorganic by-products. • Draw the product in neutral form unless conditions are clearly designed to give an ionic product. • Include cationic counter-ions, e.g., Na+ in your answer, but draw them in their own sketcher. • Do not include anionic counter-ions, e.g., I, in your answer. 90.0 ChemDoodle /n [Farrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Introductory Chemistry: A FoundationChemistryISBN:9781337399425Author:Steven S. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Introductory Chemistry: A Foundation
Chemistry
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Biomolecules - Protein - Amino acids; Author: Tutorials Point (India) Ltd.;https://www.youtube.com/watch?v=ySNVPDHJ0ek;License: Standard YouTube License, CC-BY