Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 26.SE, Problem 38AP
Show how you could prepare the following amino acids enantioselectively:
(a) Pro
(b) Val
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The structure among the following that represents an amide (peptide) bond is:
N H
N-H
-C-O-
-C-O-H
A
B
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C-0-
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structure A
structure D
structure B
structure C
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2.
Classify the following amino acids as nonpolar, polar basic, polar acidic, or polar neutral.
(a)
(b)
(c)
(d)
H₂N-CH-COH
CH-OH
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CH3
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H₂N-CH-C-OH
I
CH₂
C=O
1
OH
H₂N-CH-C-OH
CH₂
T
CH-CH3
CH₂
H₂N-CH-C-OH
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CH₂
OH
229
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.
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
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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
- Show how you would synthesize any of the standard amino acids from each starting material. You may use any necessaryreagents.O(CH3)2CH C COOH(a)CH2CH3(b) CH3 CH CH2 COOH (c) (CH3)2 CH¬CH2¬CHOarrow_forwardDraw both enantiomers of each amino acid and label them as R or S: (a) phenylalanine; (b) methionine.arrow_forwardGramicidin 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.arrow_forward
- (a) What is the difference between the hormones progesterone and testosterone? (b) Draw the structure of a a steroid nucleus. (c) Give the products obtained from complete base hydrolysis in the following reaction: O || CH,−O−C−(CH2)14–CH3 O CH–0–C−(CH2)14—CH3 + 3 NaOH O CH,−0–C−(CH2)14–CH3arrow_forwardThe dynorphins are a group of opioid peptides that play an importantrole in changes in the brain associated with cocaine addiction. One ofthese peptides, dynorphin A, contains the following amino acidsequence: Tyr–Gly–Gly–Phe–Leu–Arg–Arg–Ile–Arg–Pro–Lys–Leu–Lys.Draw the amino acids and peptide fragments formed when dynorphin A is treated with each reagent or enzyme: (a) chymotrypsin; (b) trypsin; (c)carboxypeptidase; (d) C6H5N=C=S.arrow_forwardDRAW THE CHEMICAL STRUCTURE OF THE FOLLOWING:1) Methyl 5-methyl-6-oxohexanoate2) 5-Amino-3-methylpentan-2-ol3) Isopropyl 3-hydroxypropanoate4) 3-Oxocyclohexanecarbaldehyde5) 5-Methyl-6-oxohexanamide6) p-Chloromethylbenzene7) 2,5,5-Trimethyl-4-oxohept-2-enoic acidarrow_forward
- Although only l-amino acids occur in proteins, d-amino acids are often a part of the metabolism of lower organisms. The antibiotic actinomycin D, for example, contains a unit of d-valine, and the antibiotic bacitracin A contains units of d-asparagine and d-glutamic acid. Draw Fischer projections and three-dimensional representations for these three d-amino acids.arrow_forwardGive me handwritten answer with explaination?arrow_forwardα-Amino acids can be prepared by treating an aldehyde with ammonia/trace acid, followed by hydrogen cyanide, followed by acid-catalyzed hydrolysis. What amino acid is formed when the aldehyde that is used is 3-methylbutanal?arrow_forward
- Indicate whether each statement is true or false. (a) Tryptophan is an aromatic amino acid. (b) Lysine is positively charged at pH 7. (c) Asparagine has two amide bonds. (d) Isoleucine and leucine are enantiomers. (e) Valine is probably more water-soluble than arginine.arrow_forwardanswer all the questionsarrow_forwardVasopressin is a peptide hormone synthesized by the hypothalamus; in its reduced form it has the structure shown. NH2 HS H H H H H *H3N° NH2 N' SH NH2 ОН Vasopressin NH *H2N= NH2 This structure is incorrect in that one of the amino acids is shown in the D-configuration, rather than the L-. Which one is it? What is the amino acid sequence of this peptide? Enter your answer using the single letter abbretiavions for the amino acids; i.e. GPT, not Gly-Pro-Thr. What is the net charge of this peptide at physiological pH? ZI IZ ZI IZ ZIarrow_forward
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