Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 21.4, Problem 11P
- a. Which amino acid has the lowest pI value?
- b. Which amino acid has the highest pI value?
- c. Which amino acid has the greatest amount of negative charge at pH = 6.20?
- d. Which amino acid has a greater negative charge at pH = 6.20. glycine or methionine?
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3. An amino acid has a -CH,CH3 side chain. What type of side chain could form hydrogen bonds with this side chain?
O a. -CH2-OH
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6. Is this amino acid L- or D-, and how can you tell?
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a. D-, because all amino acids are D.
b. D-, because the amine is on the right.
c. D-, because the amine is on the left.
d. L-, because the amine is on the left.
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A.
HSH,C
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H₂
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CH₂CH₂SCH₂
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Chapter 21 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 21.1 - a. Explain why, when the imidazole ring of...Ch. 21.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 21.2 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.3 - Draw the predominant form for glutamate in a...Ch. 21.3 - a. Why is the pKa of the glutamate side chain...Ch. 21.4 - Calculate the pI of each of the following amino...Ch. 21.4 - a. Which amino acid has the lowest pI value? b....Ch. 21.4 - Prob. 12P
Ch. 21.4 - Prob. 13PCh. 21.4 - Explain why the pI of lysine is the average of the...Ch. 21.5 - What aldehyde is formed when valine is treated...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.5 - Prob. 18PCh. 21.5 - Prob. 19PCh. 21.6 - Why is excess ammonia used in the preceding...Ch. 21.6 - Prob. 21PCh. 21.6 - What amino acid is formed using the...Ch. 21.6 - Prob. 23PCh. 21.6 - What amino acid is formed when the aldehyde used...Ch. 21.7 - Esterase is an enzyme that catalyzes the...Ch. 21.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 21.8 - Draw the resonance contributors of the peptide...Ch. 21.8 - Which bonds in the backbone of a peptide can...Ch. 21.9 - An opioid pentapeptide has the following...Ch. 21.9 - What is the configuration about each of the...Ch. 21.9 - Glutathione is a tripeptide whose function is to...Ch. 21.10 - What dipeptides would be formed by heating a...Ch. 21.10 - Suppose you are trying to synthesize the dipeptide...Ch. 21.10 - Show the steps in the synthesis of the...Ch. 21.10 - a. Calculate the overall yield of bradykinin when...Ch. 21.11 - Show the steps in the synthesis of the...Ch. 21.13 - Prob. 37PCh. 21.13 - In determining the primary structure of insulin,...Ch. 21.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 21.13 - Explain why cyanogen bromide does not cleave on...Ch. 21.13 - Indicate the peptides produced from cleavage by...Ch. 21.14 - Prob. 43PCh. 21.14 - Three peptides were obtained from a trypsin...Ch. 21.14 - Prob. 45PCh. 21.15 - How would a protein that resides in the nonpolar...Ch. 21.16 - a. Which would have the greatest percentage of...Ch. 21.17 - When apples that have been cut are exposed to...Ch. 21 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 21 - Prob. 50PCh. 21 - A titration curve is a plot of the pH of a...Ch. 21 - Prob. 52PCh. 21 - Aspartame (its structure is on page 1007) has a pl...Ch. 21 - Draw the form of aspartate that predominates at...Ch. 21 - Show how phenylalanine can be prepared by...Ch. 21 - A professor was preparing a manuscript for...Ch. 21 - What aldehydes are formed when the following amino...Ch. 21 - Prob. 58PCh. 21 - Determine the amino acid sequence of a polypeptide...Ch. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Which is the more effective buffer at...Ch. 21 - Identify the location and type of charge on the...Ch. 21 - Draw the product obtained when a lysine side chain...Ch. 21 - After the polypeptide shown below was treated with...Ch. 21 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 21 - Show how aspartame can be synthesized using DCCD.Ch. 21 - -Amino acids can be prepared by treating an...Ch. 21 - Reaction of a polypeptide with carboxypeptidase A...Ch. 21 - a. How many different octapeptides can be made...Ch. 21 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 21 - A mixture of 15 amino acids gave the fingerprint...Ch. 21 - Write the mechanism for the reaction of an amino...Ch. 21 - Prob. 74PCh. 21 - Show how valine can be prepared by a. a...Ch. 21 - The primary structure of -endorphin, a peptide...Ch. 21 - A chemist wanted to test his hypothesis that the...Ch. 21 - Propose a mechanism for the rearrangement of the...Ch. 21 - A normal polypeptide and a mutant of the...Ch. 21 - Determine the amino acid sequence of a polypeptide...
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- Write the General formula and Structure of the standard amino acids. D. Acids Aspartic acid (Asp,D) Glutamic acid (Glu, E) E. Bases Arginine (Ang, R) Histidine (His,H) Lysine (Lys,K) F. Aromatic Tyrosine (Tyr,T) Phenylalanine (Phe,F) Tryptophan (Trp,W) G. Amides Asparigine (Asn,N) Glutamine (Gln,Q)arrow_forward1. A. Draw the structure of L-valine in a strongly basic solution. B. What is the charge of this amino acid in a strongly basic solution?arrow_forward12) Proteins are long chains of amino acids joined together by peptide bonds. Which structure properly depicts the peptide bond formed between two generic amino acids? 12) H. R1 H;N. N, A) R1 R2 B) R2 R2 H;N, N. R1 H R2 D) ŘIarrow_forward
- 8. Hydrolysis of the peptide bonds in peptide below would result in Пн НзN-CHC-N-CHC-N-CНС-о CH2 Он СНCH3 ČH3 CH3 a. no reaction. b. a single amino acid. c. two amino acids. d. three amino acids. e. four amino acids.arrow_forwardA. Draw the structure of this amino acid in a solution of NaOH (aq) B. Draw the structure of this amino acid in a solution of H2SO4 (aq)arrow_forward4. What is the strongest type of non-covalent interactions that could form between the following amino acids' side chains? a. Valine and Alanine b. Glutamic acid and Serine c. Asparagine and Threonine d. Lysine and Aspartic acidarrow_forward
- oleic acid, linoleic acid and arachidonic acid d. arachidonic acid e. None of these are solids at room temperature. C. 21. The portion of the molecule that is boxed is called otc(CH2)16CH3 ofc(CH2)16CH3 ofċ(CH2)16CH3 || a. the amino acid backbone. b. the glycerol backbone. c. the phosphate backbone. d. a saturated fatty acid. an unsaturated fatty acid. e.arrow_forward1. Name the common amino acids that contain an aromatic ring. Enter your answers in alphabetical order separated by commas. 2. Name the common amino acids that contain sulfur. Enter your answers separated by commas. 3. Name the common amino acids that are alcohols. Enter your answers separated by commas. 4. Name the common amino acids that have alkyl-group side chains. Enter your answers separated by commas.arrow_forward3. Alanine is a diprotic amino acid. a. Make a ladder diagram for alanine. b. Draw the predominant species of alanine at pH-7.0. Draw the predominant species of alanine at pH-10.0. c.arrow_forward
- 2. Diagram the peptide ACKE at physiological then answer questions a- h. a. Circle one peptide bond. b. Box one alpha carbon in this peptide c. How many peptide bonds are present in this peptide? d. Which amino acid is at the C-terminus? e. Which amino acid is at the N-terminus? f. Label one omega, one phi and one psi bond angle. g. Sketch in one peptide plane. h. Calculate the charge of the peptide at pH 13.arrow_forwardWrite the General formula and Structure of the standard amino acids. A. Alkyl Glycine (Gly,G) Alanine (Ala,A) Valine (Val, V) Proline (Pro,P) Isoleucine (Ile,I) Leucine (Leu,L) B. Sulfur-containing Cysteine (Cys,C) Methionine (Met,M) C.Alcohols Serine (Ser,S) Threonine (Thr,T) D. Acids Aspartic acid (Asp,D) Glutamic acid (Glu, E) E. Bases Arginine (Ang, R) Histidine (His,H) Lysine (Lys,K) F. Aromatic Tyrosine (Tyr,T) Phenylalanine (Phe,F) Tryptophan (Trp,W) G. Amides Asparigine (Asn,N) Glutamine (Gln,Q)arrow_forwardA.Is glycine polar? How can you tell? B. Does a molecule have to be polar in order to be chiral? If yes, explain why chirality follows from polarity; if no, show a simple molecule that is a counterexample. C.Build alanine (chemical formula: H2NCH(CH3)COOH), which is another amino acid. Is alanine polar? Is its shape around the “central” carbon significantly different from glycine?arrow_forward
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