Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 26.5, Problem 10P
Interpretation Introduction
Interpretation:
In peptide analysis, -SH groups of cysteine are capped by SN2 reaction with iodoacetate.
Concept introduction:
In preparation for analysis, the peptide is broken into its constituent amino acids by reducing all disulfide bonds, capping the -SH groups of cysteine residues by SN2 reaction with iodoacetic acid, and hydrolyzing the amide bonds by heating with aqueous 6 M HCl at 110°C for 24 hours.
To determine:
Structure of product that would be obtained by SN2 reaction of cysteine and iodoacetic acid.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
The triple amine in an acidic medium does not give a transition n→o * Explain why?
At what pH should imine formation be carried out if the amine’s protonated form has a pKa value of 9.0?
Anilinium ion, PhNH3+ , Catalyze semicarbazone formation from benzaldhyde
much more effectively than would be expected on the basis of its strength as an acid. Explain.
Chapter 26 Solutions
Organic Chemistry
Ch. 26.1 - How many of the -amino acids shown in Table 26-1...Ch. 26.1 - Prob. 2PCh. 26.1 - Prob. 3PCh. 26.2 - Hemoglobin has pI=6.8. Does hemoglobin have a net...Ch. 26.3 - Show how you could prepare the following -amino...Ch. 26.3 - What alkyl halides would you use to prepare the...Ch. 26.3 - Prob. 7PCh. 26.4 - There are six isomeric tripeptides that contain...Ch. 26.4 - Draw the structure of M-P-V-G, and indicate its...Ch. 26.5 - Prob. 10P
Ch. 26.5 - Prob. 11PCh. 26.6 - The octapeptide angiotensin II has the sequence...Ch. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Give the amino acid sequence of hexapeptides that...Ch. 26.7 - Prob. 16PCh. 26.7 - Write all five steps required for the synthesis of...Ch. 26.10 - Prob. 18PCh. 26.SE - Identify the following amino acids:Ch. 26.SE - Prob. 20VCCh. 26.SE - Isoleucine and threonine are the only two amino...Ch. 26.SE - Prob. 22VCCh. 26.SE - Give the sequence of the following tetrapeptide:Ch. 26.SE - Prob. 24MPCh. 26.SE - The chloromethylated polystyrene resin used for...Ch. 26.SE - Prob. 26MPCh. 26.SE - Prob. 27MPCh. 26.SE - Prob. 28MPCh. 26.SE - Except for cysteine, only S amino acids occur in...Ch. 26.SE - Prob. 30APCh. 26.SE - Prob. 31APCh. 26.SE - Show the structures of the following amino acids...Ch. 26.SE - Prob. 33APCh. 26.SE - Using both three- and one-letter codes for amino...Ch. 26.SE - Prob. 35APCh. 26.SE - Show how you could use the acetamidomalonate...Ch. 26.SE - Prob. 37APCh. 26.SE - Show how you could prepare the following amino...Ch. 26.SE - Prob. 39APCh. 26.SE - Predict the product of the reaction of valine with...Ch. 26.SE - Prob. 41APCh. 26.SE - Prob. 42APCh. 26.SE - Propose two structures for a tripeptide that gives...Ch. 26.SE - Show the steps involved in a synthesis of...Ch. 26.SE - Prob. 45APCh. 26.SE - Prob. 46APCh. 26.SE - Prob. 47APCh. 26.SE - Which of the following amino acids are more likely...Ch. 26.SE - Leuprolide is a synthetic nonapeptide used to...Ch. 26.SE - The -helical parts of myoglobin and other proteins...Ch. 26.SE - Prob. 51APCh. 26.SE - Cytochrome c is an enzyme found in the cells of...Ch. 26.SE - Prob. 53APCh. 26.SE - Prob. 54APCh. 26.SE - Prob. 55APCh. 26.SE - What is the structure of a nonapeptide that gives...Ch. 26.SE - Oxytocin, a nonapeptide hormone secreted by the...Ch. 26.SE - Aspartame, a nonnutritive sweetener marketed under...Ch. 26.SE - Prob. 59APCh. 26.SE - Prob. 60APCh. 26.SE - Prob. 61APCh. 26.SE - Prob. 62AP
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
- DCC H3C ངོན་དྲིས" ",, CH3 CH3 Treatment of an α-amino acid such as alanine with DCC yields a 2,5-diketopiperazine. Draw curved arrows to show the movement of electrons in this step of the reaction mechanism. Arrow-pushing Instructions HN CH3 :0: CH3 NH HN :O: H3C N H-A NH HN CH3arrow_forwardShow how you could synthesize racemic ibuprofen starting with 1-bromo-4-isobutylbenzene.arrow_forwardWhat is the mechanism for this reaction? We get the hint that after the Grignard-reaction there is a intramolekular reaction with the ester (CO2Et-group).arrow_forward
- Provide the mechanism of the protecting group using the following reagents below.arrow_forward2) Write the products of the following reactions and indicate if they are meso compounds or racemic mixtures. + KMNO4, KOH, cold Ph Ph Ph H2, 1 atm. RT Ni (cat) Pharrow_forwardYou are planning to carry out a reaction between propyne, CH3C≡CH and sodium amide, NaNH2. You also need to choose an appropriate solvent for carrying out the reaction. Would ethanol be suitable for this purpose? Explain your rationale clearly.arrow_forward
- Please Help ASAP Predict the product/products of the following reaction. Justify your answer and show the mechanism.arrow_forward[References] All ethyl esters of long-chain aliphatic acids (for example, ethyl tetradecanoate, C13H27COOCH₂CH3) show significant fragment ions at m/z 88, 73, and 45. Draw the structure of the ion that gives the m/z 88 peak. star 14arrow_forwardGive the product of the followingarrow_forward
- We are currently working with diastereomeric products of acid-base reactions in my organic chemistry class and while I understand the basics of the creation of selectively soluble salt products, drawing the reactions has always been difficult. Our prelab asks us to "draw the expected diasteromeric products from the reaction of racemic phenylsuccinic acid with excess (s)-methylbenzylamine and label the chiral centers" I would really appreciate some help with this!arrow_forwardDoes the presence of a ring structure have any effect on the reactivity of a Sn1 reaction?arrow_forwardPlease answer this, thank u 6arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Enzymes - Effect of cofactors on enzyme; Author: Tutorials Point (India) Ltd;https://www.youtube.com/watch?v=AkAbIwxyUs4;License: Standard YouTube License, CC-BY
Enzyme Catalysis Part-I; Author: NPTEL-NOC IITM;https://www.youtube.com/watch?v=aZE740JWZuQ;License: Standard Youtube License