PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 29, Problem 29.70P
The anti-obesity drug orlistat works by irreversibly inhibiting pancreatic lipase, an enzyme responsible for the hydrolysis of triacylglycerols in the intestines, so they are excreted without
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Esterase is an enzyme that catalyzes the hydrolysis of esters. It hydrolyzes esters of L-amino acids more rapidly than esters of d-amino acids. How can this enzyme be used to separate a racemic mixture of amino acids?
Gramicidin S, a topical antibiotic produced by the bacterium Bacillus brevis, is a cyclic decapeptide formed from five amino acids. Draw the structures of the amino acids that form gramicidin S, and explain why this compound possesses two unusual structural features.
The first step in the catabolism of most amino acids is the removal of the nitrogen atom by transfer to an a-keto acid, a reaction
catalyzed by an enzyme called a transaminase. The a-keto acid acceptor is often a-ketoglutarate. Modify the structures in the
product to show the products of the transamination of cysteine. Be sure to show functional groups with the charge and number of
attached hydrogen atoms appropriate for pH 7.4.
transaminase
+
O=C
H₂N-CH
+
CH₂
CH₂
CH₂
SH
Incorrect
H₂N
||
CH
|
CH₂
|
CH₂
I
||
O
||
n
|
CH₂
T
SH
Chapter 29 Solutions
PKG 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
- Triosephosphate isomerase (TIM) catalyzes the conversion of dihydroxyacetone phosphate to glyceraldehyde-3-phosphate. The enzyme’s catalytic groups are Glu 165 and His 95. In the first step of the reaction, these catalytic groups function as a general-base and a general-acid catalyst, respectively. Propose a mechanism for the reaction.arrow_forwardChemistry Describe two chemical strategies that have been employed to try to overcome the problem of penicillin-based antibiotics susceptibility to β-Lactamases.arrow_forwardIf an enzyme-catalyzed reaction has a high rate at low pH and low rate at higher pH, this implies that a group on either the enzyme or the substrate must be for an efficient reaction. leaving group oxidoreductase coenzymes O protonated deprotonated The compound that consists of deoxyribose linked by an N-glycosidic bond to N-9 of guanine is: adenylate deoxyguanosine guanosine nucleotide guanylatearrow_forward
- Treating 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_forwardResearchers analysed a glycopeptide (a peptide carrying one or several oligosaccharide groups) and determined both the sequence of the peptide and the sequence of the sugar molecule. The latter was identified as a diholoside coupled to the peptide by an osidic bond. The systematic name of this sugar is: B-D-glucopyranosyl-(1→4)-ß-D-galactopyranose. : Represent the chemical formula of this diholoside in a way that all oses are Question 1 represented according to the Haworth convention. Apart from the furane and/or pyrane cycles all atoms of this molecule must be given.arrow_forwardIdentify the organic functional group and reaction type for the following reaction. The reactant is a(n) - carboxylic acid hexose - Aldohexose - aldotetrose -deoxyhexose -carboxylic acid tetrose - ketohexose The product is a(n) - carboxylic acid tetrose - aldotetrose -alcohol hexose -aldohexose -carboxylic acid hexose - alcohol tetrose The reaction type is - hemiacetal formation -hydrolysis -oxidation( Benedict’s) -acetal formation -reduction( hydrogenation) - mutarotationarrow_forward
- Explain in a more clinical detail the mode of actions of the following on the human skin cell or tissue: 1. FREE-RADICAL2. ANTI-OXIDANTS3. PEPTIDES AND PROTEINSarrow_forwardWhich is true about the ß-lactam compounds? their pharmacophore has five-membered ring structure they work only on Gram-negative bacteria O they work as inhibitor in cell membrane synthesis O they are irreversible inhibitors of the bacterial serine proteasearrow_forwardWhat is the general role of enzymes in the human body?arrow_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
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
General, Organic, and Biological Chemistry
Chemistry
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:Cengage Learning
Organic And Biological Chemistry
Chemistry
ISBN:9781305081079
Author:STOKER, H. Stephen (howard Stephen)
Publisher:Cengage Learning,
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
DIGESTER-35 | VITAMINS AND THEIR RELATED COENZYMES| GPAT | NIPER | PHARMACIST| DI; Author: GPAT DISCUSSION CENTER;https://www.youtube.com/watch?v=CGrdNYmho0s;License: Standard YouTube License, CC-BY