Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 29, Problem 29.67P
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 29.67P, 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 29.67P, 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)
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1. Biogenic Amines are inactivated primarily by
a. Sulfonation
b. Glucoronidation
c. Aromatic hydroxylation
d. Methylation
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c. Free drug
d. Both B & C
e. Both A & C
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a. Capsule
b. Tablet
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a. Solubility increase with decrease particle size
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5. The rate in which the drug appears in the bloodstream is also known as
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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?
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Chapter 29 Solutions
Organic Chemistry-Package(Custom)
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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