EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 21, Problem 76P
The primary structure of β-endorphin, a peptide containing 31 amino acids synthesized by the body to control pain, is shown here:
Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-He-He-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu
- a. What fragments are obtained as a result of treatment with each of the following?
1. trypsin
2. cyanogen bromide
3. chymotrypsin
- b. How much of the primary structure can be determined if the amino acids contained in each fragment (but not their sequence ) are known?
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The primary structure of b-endorphin, a peptide containing 31 amino acids synthesized by the body to control pain, is shown here:
Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr- Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu
How much of the primary structure can be determined if the amino acids contained in each fragment (but not their sequence) are known?
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
ZI
Estimate the isoelectric point of aspartame
Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
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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- What amino acid sequence is coded by the following mRNA base sequence? CUU-AUG-GCU-UGG-CCC-UAAarrow_forwardFollowing is the primary structure of glucagon, a polypeptide hormone of 29 amino acids. Glucagon is produced in the -cells of the pancreas and helps maintain blood glucose levels in a normal concentration range. Which peptide bonds are hydrolyzed when this polypeptide is treated with each reagent? (a) Phenyl isothiocyanate (b) Chymotrypsin (c) Trypsin (d) BrCNarrow_forwardIdentify one amino acid from each of the following categories: H2N -CH OH H2N -CH- C OH H2N -CH HO- I II III CH2 CH2 CH—ОН CH3 CH3 OH H2N -CH- HO- H2N FCH -C- HO- CH2 H2N-CH- c-OH CH2 CH2 CH2 S CH2 CH3 CH3 IV V VI (a) One amino acid that is likely to have a net negative charge at pH 8. (b) One amino acid that may be dehydrated with H2SO4. (c) One polar uncharged amino acid. (d) One nonpolar aromatic amino acid. (e) The nonpolar amino acid with the highest molar mass that was not previously selected.arrow_forward
- Which structure below contains a peptide bond? H H2N FHÇ HO- CH3 O CH3 H2N -CH- CFOH CH3 H2N -CH2- --O NH CH3arrow_forward5.Indicate the amino acid as polar or nonpolar OH CH: 0 H₂N-C-C-OH H O CH, 0 !! H₂N-C-C-o H CH3 CH3 CH CHO 11₂N-C-C-07 H 6) Acids and bases denature a protein by disrupting A) peptide bonds and ionic bonds. B) amide bonds and alkene bonds. C) hydrophobic interactions and peptide bonds. D) ionic bonds and hydrophobic interactions. E) ionic bonds and hydrogen bonds. 5) Heat denatures a protein by disrupting A) ionic bonds and peptide bonds. B) hydrophobic bonds and hydrogen bonds. C) peptide bonds and hydrophobic bonds. D) disulfide bonds and peptide bonds. E) hydrogen bonds and disulfide bonds. 7) Denaturation of a protein A) changes the primary structure of a protein. B) disrupts the secondary, tertiary, or quaternary structure of a protein. C) is always irreversible. D) hydrolyzes peptide bonds. E) can only occur in a protein with quaternary structure. 8) Heavy metals denature proteins by A) releasing amino acids. B) disrupting hydrophobic interactions. C) changing the pH of the…arrow_forwardNet charge and isoelectric point of an amino acid with an ionizable side group.Consider the net charge and isoelectric point of an amino acid with ionizable side (R-) group.(a) Identify the acidic amino acid(s) capable of having a negatively charged carboxyl side group.(b) Identify the basic amino acid(s) capable of having a positively charged amino side group.(c) For an amino acid with a side (R-) chain that can ionize to a negative charge, derive a general expression in terms of measured pH and known pKa values of α-carboxyla-amino (pKca), α-amino(pKaa),and side group (pKRa), respectively, for the net charge of an amino acid Consider the net charge and isoelectric point of an amino acid with ionizable side (R-) group.(d) For an amino acid with a side (R-) chain that can ionize to a positive charge, derive a general expression in terms of measured pH and known pKa values ofα-carboxyl (pKca), α-amino (pKaa), and side group (pKRa), respectively, for the net charge of the amino acid.(e)…arrow_forward
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