ORGANIC CHEMISTRY-EBOOK>I<
9th Edition
ISBN: 9781305084414
Author: McMurry
Publisher: INTER CENG
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 28.SE, Problem 20MP
One of the steps in the biosynthesis of uridine monophosphate is the reaction of aspartate with carbamoyl phosphate to give carbamoyl aspartate followed by cyclization to form dihydroorotate. Propose mechanisms for both steps.
![Chapter 28.SE, Problem 20MP, One of the steps in the biosynthesis of uridine monophosphate is the reaction of aspartate with](https://content.bartleby.com/tbms-images/9781305080485/Chapter-28/images/80485-28.se-20mp-question-digital.jpg)
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Trending nowThis is a popular solution!
![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
There is a tick and mosquito repellent DEET (diethyltoluamide) that is prepared by a reaction of diethylamine with m-methylbenzomic acid (m-toluic acid) H+ and heat. What's the structure of DEET?
A variation of the acetamidomalonate synthesis can be used to synthesize serine. The process involves the following steps:
Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1;
Enolate anion 1 makes a nucleophilic attack on formaldehyde, forming tetrahedral intermediate 2;
Protonation of the oxyanion forms alcohol 3;
Acid hydrolysis yields dicarboxyamino alcohol 4;
Decarboxylation leads to the final amino acid.
Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2.
You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
Do not include lone pairs in your answer. They will not be considered in the grading.
Draw carboxyl and amino groups in their uncharged forms.
An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glu (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile–Leu in addition to other products. Deduce the structure of the octapeptide and fragments A–D.
Chapter 28 Solutions
ORGANIC CHEMISTRY-EBOOK>I<
Ch. 28.1 - Draw the full structure of the DNA dinucleotide...Ch. 28.1 - Draw the full structure of the RNA dinucleotide...Ch. 28.2 - What sequence of bases on one strand of DNA is...Ch. 28.4 - Show how uracil can form strong hydrogen bonds to...Ch. 28.4 - What RNA base sequence is complementary to the...Ch. 28.4 - From what DNA base sequence was the following RNA...Ch. 28.5 - List codon sequences for the following amino...Ch. 28.5 - List anticodon sequences on the tRNAs carrying the...Ch. 28.5 - What amino acid sequence is coded by the following...Ch. 28.5 - What is the base sequence in the original DNA...
Ch. 28.7 - Prob. 11PCh. 28.7 - Prob. 12PCh. 28.SE - Identify the following bases, and tell whether...Ch. 28.SE - Identify the following nucleotide, and tell how it...Ch. 28.SE - Amine bases in nucleic acids can react with...Ch. 28.SE - The final step in DNA synthesis is deprotection by...Ch. 28.SE - The final step in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of a...Ch. 28.SE - One of the steps in the metabolic degradation of...Ch. 28.SE - One of the steps in the biosynthesis of uridine...Ch. 28.SE - Human brain natriuretic peptide (BNP) is a small...Ch. 28.SE - Human and horse insulin both have two polypeptide...Ch. 28.SE - The DNA of sea urchins contains about 32% A. What...Ch. 28.SE - The codon UAA stops protein synthesis. Why does...Ch. 28.SE - Which of the following base sequences would most...Ch. 28.SE - For what amino acids do the following...Ch. 28.SE - Prob. 27APCh. 28.SE - Prob. 28APCh. 28.SE - Draw the complete structure of the ribonucleotide...Ch. 28.SE - Draw the complete structure of the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - Give an mRNA sequence that will code for the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - What amino acid sequence is coded for by the...Ch. 28.SE - Prob. 35APCh. 28.SE - Show the steps involved in a laboratory synthesis...Ch. 28.SE - Draw the structure of cyclic adenosine...Ch. 28.SE - Prob. 38AP
Additional Science Textbook Solutions
Find more solutions based on key concepts
What is the pH range for acidic solutions? For basic solutions?
EBK INTRODUCTION TO CHEMISTRY
Determine the de Brogue wavelength of a. an electron moving at 1/10 the speed of light. b. a 400 g Frisbee movi...
Inorganic Chemistry
Determine the number of protons, neutrons, and electrons in the following atoms: a. a hydrogen atom that has a ...
General, Organic, and Biological Chemistry (3rd Edition)
What is the pH range for acidic solutions? For basic solutions?
Introduction to Chemistry
The method to determine the volume of a powered solid, liquid and a rock needs to be determined. Concept introd...
Living By Chemistry: First Edition Textbook
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
- Trimyristin is obtained from coconut oil and has the molecular formula C45H86O6. On being heated with aqueous sodium hydroxide followed by acidification, trimyristin was converted to glycerol and tetradecanoic acid as the only products. What is the structure of trimyristin?arrow_forwardCarboxylic acid is treated with an alcohol and an acid catalyst, an ester is formed and this reaction is called the Fischer esterification. From the reaction, propose the mechanism of ester esterification and ester hydrolysis and their relationshiparrow_forwardNucleosides are stable in water and in dilute base. In dilute acid, however, the glycosidic bond of a nucleoside undergoes hydrolysis to give a pentose and a heterocyclic aromatic amine base. Propose a mechanism for this acid-catalyzed hydrolysis.arrow_forward
- Identify 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_forwardDescribe the hydrolysis reaction of aspartame after the treatment of acid (HCl) and base (NaOH).Write down the mechanism and identify the compounds.arrow_forwardWhat is the product of the starting material D-glyceraldehyde which will (1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3 (2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3arrow_forward
- 3a. 3b. 3c 3d. 3e. CO₂ clavulanic acid CH₂-OH H Answer the following questions about clavulanic acid. Does clavulanic acid inhibit D-alanyl-D-alanine transpeptidase? Does clavulanic acid contain a ß-lactam? Does clavulanic acid contain a thiazolium ring? What is the result of the treatment of penicillinase with clavulanic acid? Does clavulanic acid form a covalent acyl-enzyme intermediate with penicillinase?arrow_forwardKojibiose is a reducing sugar that forms D-glucose on hydrolysis with aqueous acid. Reaction of kojibiose with iodomethane and Ag20 yields an octamethyl derivative, which can be hydrolyzed with aqueous acid to give one equivalent of 2,3,4,6-tetra-O- methyl-D-glucopyranose and one equivalent of 3,4,6-tri-O-methyl-D-glucopyranose. If kojibiose is hydrolyzed by alpha-glucosidases but not beta-glucosidases, what is its structure?arrow_forwardThe 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 SHarrow_forward
- Prostaglandins are a class of eicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax Km = mM/min mMarrow_forwardThe first step in the metabolism of glycerol, formed by digestion of fats, is phosphorylation of the pro-R—CH2OH group by reaction with adenosine triphosphate (ATP) to give the corresponding glycerol phosphate plus adenosine diphosphate (ADP). Show the stereochemistry of the product.arrow_forwardIn dilute aqueous base, (R)-glyceraldehyde is converted into an equilibrium mixture of (R,S)-glyceraldehyde and dihydroxyacetone. Propose a mechanism for this isomerization.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
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
CBSE Class 12 Chemistry || Polymers || Full Chapter || By Shiksha House; Author: Best for NEET;https://www.youtube.com/watch?v=OxdJlS0xZ0Y;License: Standard YouTube License, CC-BY