Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 26.SE, Problem 29AP
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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The configuration of the chiral center in a-amino acids is most commonly specified using the d,l convention. It can also be identified using the R,S convention . Does the chiral center in l-serine have the R or S configuration?
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.
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1a. The lack of an asymmetric carbons and ease of rotation make glycine rich protein sequences:
a. Fibrous
b. Helical
c. Cyclic
d. Flexible
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a. Change pKa
b. Reduce thermal stability
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d. Slow degradation
e. Increase solubility
1c. Cellulose is not useful dietary carbohydrate because humans:
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b. Lack a 1,4-beta glycosidase
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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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- Assign R or S configuration to each chirality center in the following molecular model of the amino acid isoleucine (blue = N):arrow_forwardPart C. Give the structure of the following and encircle the peptide bond 1. Glycyl - Seryl - Valine 2. Alanyl - Isoleucine 3. Prolyl - Leucine 4. Methionyl - Aspargyl - Glycine 5. Glutamyl - Methionyl - Isoleucine Part D. Draw the structure 1. L valine 2. L leucine 3. L serine 4. D aspartic acid 5. D glycinearrow_forwardDraw the R absolute configuration of lysine.arrow_forward
- Different Ways of Drawing an Enantiomer Locate the stereogenic center in the amino acid alanine, and draw the enantiomer using the two methods shown in Figure 5.5.arrow_forwardDraw the stereoisomers of the following amino acids. Indicate pairs of enantiomers and pairs of diastereomers.arrow_forwardDraw three-dimensional representations of the following amino acids.(a) l-phenylalaninearrow_forward
- 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.arrow_forward16*32 Many tumors of the breast are correlated with estrogen levels in the body. Drugs that interfere with estrogen binding have antitumor activity and may even help prevent tumor occurrence. A widely used antiestrogen drug is tamoxifen. kJ1 Name the functional groups in tamoxifen. Classify the amino group in tamoxifen as primary, secondary, or tertiary. How many stereoisomers are possible for tamoxifen? (d, Would you expect tamoxifen to be soluble or insoluble in water? In blood?arrow_forwardAs stated, proteins are stereochemically pure because only a single enantiomer of each amino acid building block is used by nature. How many stereoisomers are possible for a chain of only 3 chiral amino acids if both enantiomers of the amino adds are used? 1. 2 2. 4 3. 8 4. 16arrow_forward
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