Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 17.10, Problem 22P
Interpretation Introduction
Interpretation:
The sequence of given decapeptide has to be given with the help of given fragments.
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A decapeptide undergoes partial hydrolysis to give peptides whose amino acid compositions are shown. Reaction of the intact decapeptide with Edman’s reagent releases PTH-Gly. What is the sequence of the decapeptide? 1. Ala, Trp 3. Pro, Val 5. Trp, Ala, Arg 7. Glu, Ala, Leu
2. Val, Pro, Asp 4. Ala, Glu 6. Arg, Gly 8. Met, Pro, Leu, Glu
Draw the structure of each peptide. Label the N-terminal and C-terminal amino acids and all amide
bonds.
a. Val-Glu
b. Gly-His-Leu
c. M-A-T-T
The pka's of the amino acid asparagine are 2.02 and 8.80. Select the asparagine structure
that predominates at pH 10.
Structure b
Structure a
Structure c
Structure di
NH,
NH,
Chapter 17 Solutions
Essential Organic Chemistry, Global Edition
Ch. 17.1 - a. Explain why, when the imidazole ring of...Ch. 17.2 - Prob. 2PCh. 17.3 - Prob. 3PCh. 17.3 - Prob. 4PCh. 17.3 - Prob. 6PCh. 17.4 - Calculate the pI of each of the following amino...Ch. 17.4 - a. Which amino acid has the lowest pI value? b....Ch. 17.5 - What aldehyde is formed when valine is treated...Ch. 17.5 - Prob. 10PCh. 17.5 - Prob. 11P
Ch. 17.5 - Prob. 12PCh. 17.6 - Prob. 13PCh. 17.6 - What amino acid would be formed using the...Ch. 17.6 - What amino acid would be formed when the aldehyde...Ch. 17.7 - Pig liver esterase is an enzyme that catalyzes the...Ch. 17.8 - Prob. 17PCh. 17.8 - Prob. 18PCh. 17.8 - Prob. 19PCh. 17.8 - Prob. 20PCh. 17.10 - Prob. 21PCh. 17.10 - Prob. 22PCh. 17.10 - Why does cyanogen bromide not cleave on the C-side...Ch. 17.10 - Prob. 24PCh. 17.10 - Prob. 26PCh. 17.12 - Prob. 27PCh. 17.13 - a. Which would have the greatest percentage of...Ch. 17 - Draw the predominant form of the following amino...Ch. 17 - What is the pI of serine?Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Which would have a higher percentage of negative...Ch. 17 - Draw the form of aspartate that predominates at...Ch. 17 - Prob. 35PCh. 17 - A professor was preparing a manuscript for...Ch. 17 - a. Why is the pKa of the glutamate side chain...Ch. 17 - Prob. 38PCh. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 40PCh. 17 - Prob. 41PCh. 17 - Three peptides were obtained from a trypsin...Ch. 17 - Prob. 43PCh. 17 - After the polypeptide shown here was treated with...Ch. 17 - The disulfide bridges of a polypeptide were...Ch. 17 - -Amino acids can be prepared by treating an...Ch. 17 - Reaction of a polypeptide with carboxypeptidase A...Ch. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Show how valine can be prepared by a. a Strecker...Ch. 17 - Prob. 51PCh. 17 - Why is proline never found in an -helix?Ch. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 55PCh. 17 - A chemist wanted to test his hypothesis that the...Ch. 17 - A normal polypeptide and a mutant of the...
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- Vasopressin 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_forwardWhich amino acid has a negative charge at physiological pH? H₂N- NH3 CH₂ CH₂ CH₂ CH₂ C-COO™ H Lysine (Lys, K) serine H₂N- C-COO H O glycine O lysine H Glycine (Gly, G) aspartate C .O. CH₂ H₂N- C -COO™ H Aspartate (Asp, D) OH CH₂ H₂N-C- -COO™ H Serine (Ser, S)arrow_forwardC. AMINO ACIDS AND PEPTIDES Consider the structure of the peptide, Asn-Gln-Gly-Ala. H₂N. OH Asn-Gln-Gly-Ala NH₂ 1. How many peptide bonds are present? 2. What is the N-terminal amino acid? Provide the three-letter name. 3. What is the C-terminal amino acid? Provide the three-letter name. H₂N,arrow_forward
- Calculate the isoelectric point for each amino acid.a. cysteine: pKa (COOH) = 2.05; pKa (a-NH3+) = 10.25b. methionine: pKa (COOH) = 2.28; pKa (a-NH3+) = 9.21arrow_forwardConsider the structures of the two amino acids below. Draw a dipeptide (peptide made from two amino acids) with Lysine as the N-terminal residue, and Tyrosine as the C-terminal residue. H. H2N-C-COOH H2N-C-COOH CH2 CH2 CH2 CH2 CH2 NH2 ОН lysine tyrosinearrow_forward1. A given glycine solution was titrated against NaOH and pH of the final solution was 4.8. Given that pKa1 and pKa2 of glycine are 2.34 and 9.60, respectively. Calculate the concentration of the dissociated amino acid in terms of the undissociated amino acid, if [x] and [y] are the concentrations of dissociated and undissociated amino acid, respectively.arrow_forward
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