Bundle: Organic Chemistry, 9th, Loose-Leaf + OWLv2, 4 terms (24 months) Printed Access Card
9th Edition
ISBN: 9781305701021
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 26.SE, Problem 57AP
Oxytocin, a nonapeptide hormone secreted by the pituitary gland, functions by stimulating uterine contraction and lactation during childbirth. Its sequence was determined from the following evidence:
1. Oxytocin is a cyclic compound containing a disulfide bridge between two cysteine residues.
2. When the disulfide bridge is reduced, oxytocin has the constitution Asn, Cys2, Gln, Gly, Ile, Leu, Pro, Tyr.
3. Partial hydrolysis of reduced oxytocin yields seven fragments:
Asp-Cys, Ile-Glu, Cys-Tyr, Leu-Gly, Tyr-Ile-Glu, Glu-Asp-Cys, and Cys-Pro-Leu.
4. Gly is the C-terminal group.
5. Both Glu and Asp are present as their side-chain amides (Gln and Asn) rather than as free side-chain acids.
What is the amino acid sequence of reduced oxytocin? What is the structure of oxytocin itself?
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Students have asked these similar questions
(28 pts.) 7. Propose a synthesis for each of the following transformations. You must include the
reagents and product(s) for each step to receive full credit. The number of steps is provided.
(OC 4)
4 steps
4 steps
OH
b.
LTS
Solid:
AT=Te-Ti
Trial 1
Trial 2
Trial 3
Average
ΔΗ
Mass water, g
24.096
23.976
23.975
Moles of solid, mol
0.01763
001767
0101781
Temp. change, °C
2.9°C
11700
2.0°C
Heat of reaction, J
-292.37J -170.473
-193.26J
AH, kJ/mole
16.58K 9.647 kJ 10.85 kr
16.58K59.64701
KJ
mol
12.35k
Minimum AS,
J/mol K
41.582
mol-k
Remember: q = mCsAT (m = mass of water, Cs=4.184J/g°C) & qsin =-qrxn &
Show your calculations for:
AH in J and then in kJ/mole for Trial 1:
qa (24.0969)(4.1845/g) (-2.9°C)=-292.37J
qsin =
qrxn =
292.35 292.37J
AH in J = 292.375 0.2923kJ
0.01763m01
=1.65×107
AH in kJ/mol =
=
16.58K
0.01763mol
mol
qrx
Minimum AS in J/mol K (Hint: use the average initial temperature of the three trials, con
Kelvin.)
AS=AHIT
(1.65×10(9.64×103) + (1.0
Jimai
For the compound: C8H17NO2
Use the following information to come up with a plausible structure:
8
This compound has "carboxylic acid amide" and ether functional groups.
The peaks at 1.2ppm are two signals that are overlapping one another.
One of the two signals is a doublet that represents 6 hydrogens; the
other signal is a quartet that represents 3 hydrogens.
Chapter 26 Solutions
Bundle: Organic Chemistry, 9th, Loose-Leaf + OWLv2, 4 terms (24 months) Printed Access Card
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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