EP ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582453
Author: Brown
Publisher: Cengage Learning
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Question
Chapter 27, Problem 27.19P
Interpretation Introduction
Interpretation:
The amino acid which is the precursor of the histamine molecule has to be given and the organic reaction involved in the biosynthesis of histamine from the amino acid has to be given.
Concept Introduction:
Decarboxylation is a
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Students have asked these similar questions
There are 20 common, naturally occurring amino acids from which all proteins are derived (as will be discussed in Chapter 25),
although many other less common amino acids have been isolated from natural sources. Valine is one of the 20 common amino acids,
and it was used as a starting material in the laboratory synthesis of an uncommon amino acid (Tetrahedron 1997, 53, 1151-1156).
During one of the steps in the synthesis, compound 1 was treated with HBr under conditions that favor radical addition, giving
stereoisomers 2 and 3. Draw the structures of 2 and 3, and describe their stereoisomeric relationship.
H.
LOCH3
HBr
2 + 3
hv
H
(S)-valine
Modify the given copies of compound 1 to drawthe structures of 2 and 3. You can use the single bond tool to add/remove double
bonds.
CH2
CH2
H,C-
H3C-
-CH,
-CH,
Edit Drawing
Describe the relationship of 2 and 3.
O They are enantiomers.
O They are superimposable.
They are diastereomers.
O They are constitutional isomers.
What is the Answer for (a.) ?
refer to (Org. Lett. 2021, 23, 6278−6282).
Chapter 27 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 27.1 - Of the 20 protein-derived amino acids shown in...Ch. 27.2 - Prob. 27.2PCh. 27.2 - Prob. 27.3PCh. 27.3 - Draw a structural formula for Lys-Phe-Ala. Label...Ch. 27.4 - Which of these tripeptides are hydrolyzed by...Ch. 27.4 - Deduce the amino acid sequence of an undecapeptide...Ch. 27.6 - Prob. 27.7PCh. 27 - What amino acid does each abbreviation stand for?...Ch. 27 - The configuration of the chiral center in -amino...Ch. 27 - Assign an R or S configuration to the chiral...
Ch. 27 - Prob. 27.11PCh. 27 - Prob. 27.12PCh. 27 - Draw zwitterion forms of these amino acids. (a)...Ch. 27 - Prob. 27.14PCh. 27 - Why is Arg often referred to as a basic amino...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Prob. 27.18PCh. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Both norepinephrine and epinephrine are...Ch. 27 - Prob. 27.22PCh. 27 - Draw a structural formula for the form of each...Ch. 27 - Prob. 27.24PCh. 27 - Write the zwitterion form of alanine and show its...Ch. 27 - Prob. 27.26PCh. 27 - Write the form of aspartic acid most prevalent at...Ch. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - For lysine and arginine, the isoelectric point,...Ch. 27 - Prob. 27.31PCh. 27 - Account for the fact that the isoelectric point of...Ch. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - At pH 7.4, the pH of blood plasma, do the majority...Ch. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - A chemically modified guanidino group is present...Ch. 27 - Draw a structural formula for the product formed...Ch. 27 - Prob. 27.41PCh. 27 - Prob. 27.42PCh. 27 - A decapeptide has the following amino acid...Ch. 27 - Following is the primary structure of glucagon, a...Ch. 27 - Prob. 27.45PCh. 27 - Draw a structural formula of these tripeptides....Ch. 27 - Estimate the pI of each tripeptide in Problem...Ch. 27 - Glutathione (G-SH), one of the most common...Ch. 27 - Following are a structural formula and a...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - Prob. 27.52PCh. 27 - Prob. 27.53PCh. 27 - Prob. 27.54PCh. 27 - Distinguish between intermolecular and...Ch. 27 - Prob. 27.56PCh. 27 - Prob. 27.57P
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- On complete hydrolysis, a polypeptide gives two alanine, one leucine, one methionine, one phenylalanine, and one valine residue. Partial hydrolysis gives the following fragments: Ala-Phe, Leu-Met, Val-Ala, Phe-Leu. It is known that the first amino acid in the sequence is valine and the last one is methionine. What is the complete sequence of amino acids?arrow_forwardDraw the tetrapeptide below out in full chemical structure by attaching the four amino acidsin order (this is an application of the characteristicorganic reaction Formation of an Amide. You can use any chemical notation orcombination of notations to draw your structure, but all bonds and atoms must be shown. Tyr-Cys-Met-Hisarrow_forwardWhich of the common amino acids is not chiral? Sketch its structure and explain why it does not manifest chirality.arrow_forward
- Outline the four general stages in an enzyme-catalyzedreaction.arrow_forward8. (a) What are cardiac glycosides? Give one example of cardiac glycoside and draw structure. Discuss the structure- activity relationship of cardiac glycosides.arrow_forwardWhat special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forward
- Consider the tripeptide leucylvalyltryptophan. a. Specify its structure using three-letter symbols for the amino acids. b. How many peptide bonds are present within the peptide? c. Which of the amino acid residues has the largest R group? d. Which of the amino acid residues, if any, has a basic side chain?arrow_forwardFor the tripeptide GlyAlaCys a. What amino acid is located at the peptides N-terminal end? b. What amino acid is located at the peptides C-terminal end? c. How many peptide bonds are present? d. How many amide linkages are present?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
- Consider the tripeptide tyrosylleucylisoleucine. a. Specify its structure using three-letter symbols for the amino acids. b. How many peptide bonds are present within the peptide? c. Which of the amino acid residues has the largest R group? d. Which of the amino acid residues, if any, has an acidic side chain?arrow_forwardCompare the structures of the peptide neurotransmitters Met-enkephalin and Leu-enkephalin in terms of a. what they have in common. b. how they differ.arrow_forward22-48 How many amino acid residues in the A chain of insulin are the same in insulin from humans, cattle (bovine), hogs, and sheep?arrow_forward
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