Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 26.SE, Problem 21VC
Isoleucine and threonine are the only two amino acids with two chirality centers. Assign R or S configuration to the methyl-bearing carbon atom of isoleucine.
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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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What is the isoelectric point for the peptide MNPQR at pH 7? Draw the structure, including the stereochemistry of each C-alpha chiral center.
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Valine has pKa's of 2.286 and 9.719. Estimate the fractional composition of Valine in the -1 form at pH=6.
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Draw the structure of the amino acid L-leucine at each pH: (a) 6; (b) 10; (c) 2. Which form predominates at L-leucine's isoelectric point?
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The pKa for the side chain amino group in lysine is 10.4. If we were working at physiological pH 7.4, what would be the ratio of the protonated to unprotonated versions of lysine?
a.
1000:1
b.
3:1
c.
1:1000
d.
1:3
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An amino acid's guadinine side chain has a pKa of 12.5
what is the ratio of uncharged to charged guanidino at pH10.5
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Draw the structure of the most prominent form of tyrosine at pH 1.9
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What is the predominant form of the following amino acids at pH= 11? What is the overall charge on the amino acid?
valine
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The isoelectric point of glutamic acid is pH 3.22. What is the structure of the major form of glutamic acid at pH values of: 1.00, 3.22 and 11.00?
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25. The amino acid side chains of 17 of the 20 most common amino acids are shown below. Which side chains are considered to be acidic? Which side chains contain aromatic amines?
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Answer the following questions about the amino acid whose Fischer projection formula is a. Is it a D-amino acid or an L-amino acid? b. Is it a nonpolar or polar amino acid? c. Is it an essential or nonessential amino acid? d. Is it a standard or nonstandard amino acid?
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Except for cysteine, only S amino acids occur in proteins. Several R amino acids are also found in nature, however. (R)-Serine is found in earthworms, and (R)-alanine is found in insect larvae. Draw Fischer projections of (R)-serine and (R)-alanine. Are these d or l amino acids?
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