Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 26.SE, Problem 20VC
Interpretation Introduction
Interpretation:
The amino acids join together using the amide bond and the structure can be shown using the 3D representation with ball and stick form.
Concept introduction:
The amino acids join together by formation of amide bond, where the carboxyl group of one amino acid binds with the
To determine:
Sequence of the given tetrapeptide sequence.
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Students have asked these similar questions
A tripeptide contains lysine (R= -(CH₂)4NH₂), phenylalanine (R= -CH₂C6H5) and glycine (R= -H). It was found that the tripeptide reacts with 2 moles
of DNFB to give compound A. When compound A was treated with SOCI2, glycine was activated. When hydrolyzed, both NH₂ groups of lysine were
found to be DNP-labelled. What is the structure of the tripeptide?
Select one:
H
(CH₂)2NH2
CH
NH
CH
H₂N
O
O
H₂N
H₂N
H₂N
C
(CH2)4NH2
CH
010
(CH2)4NH2
CH
C=O
CH,Ph
CH
NH
NH
NH
CH
CH,Ph
CH
H
010
CH
CH,Ph
CH
(CH2)4NH2
ΝΗ
NH
NH
NH
CH,Ph
CH
H
CH
COOH
H
CH
COOH
COOH
COOH
Which dipeptide(s), (i)-(iv), may be formed in the reaction of
glycine and phenylalanine?
Glycine Phenylalanine
H2N-
CH2-
COOH
(0
CH-
CH
OH
(M)
K-CH
CHy-C-OH
HN-
CH-C
CH-N-N-
Ph
O ) only
O (ii) only
KO ) and (iv)
O ) and (ii)
iM only
None
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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- Give the sequence of the following tetrapeptide:arrow_forwardThe amino acids tyrosine, lysine and glycine are constituents of many proteins. HN CH COH CH₂ =0 H₂N-CH-C-OH OH tyrosine (CH₂) NH2 lysine H₂N CH-C-OH H glycine (a) State the reagents and conditions you could use to break proteins down into amino acids. (b) Draw a ring around each chiral centre in the above molecules. [2] [1] (c) In aqueous solution amino acids exist as zwitterions. Draw the zwitterionic structure of glycine. .[1] (d) For each of the following reactions, draw the structure of the organic compound formed. (i) glycine + excess NaOH(aq) (ii) tyrosine + excess NaOH(aq)arrow_forwardConsider the R groups of the following amino acids: cysteine: -CH₂SH; alarine -CH seine -CH₂OH The name for the dipeptide shown below is CH3 0 NHẠCH-C-NHCHCH O seryl-cysteine O alanyl-serine CH₂OH O seryl-alanine O serine-alanine O alanyl-cysteinearrow_forward
- An octapeptide contains the following amino acids: Arg, Glu, His, Ile, Leu, Phe, Tyr, and Val. Carboxypeptidase treatment of the octapeptide forms Phe and a heptapeptide. Treatment of the octapeptide with chymotrypsin forms two tetrapeptides, A and B. Treatment of A with trypsin yields two dipeptides, C and D. Edman degradation cleaves the following amino acids from each peptide: Glu (octapeptide), Glu (A), Ile (B), Glu (C), and Val (D). Partial hydrolysis of tetrapeptide B forms Ile–Leu in addition to other products. Deduce the structure of the octapeptide and fragments A–D.arrow_forwardA) Draw the structure of the peptide Methionylleucyltyrosylasparagine in the zwitterion form: Tyrosine: R=-CH₂- -OH Methionine: R=CH₂-CH₂-S-CH₂ Asparagine: R=-CH₂-C-NH₂ Leucine: R=-CH₂-CH-CH₂ B) Classify the following amino acids as polar, nonpolar, acidic or basic: Tyrosine: Leucine: CHSarrow_forwardCalculate an approximate pI for Peptide E-G-E-Aarrow_forward
- Give the amino acid sequence of an octapeptide that contains the amino acids Tyr, Ala, Leu (2 equiv), Cys, Gly, Glu, and Val, and forms the following fragments when partially hydrolyzed with HCl: Val–Cys–Gly–Glu, Ala–Leu–Tyr, and Tyr–Leu–Val–Cys.arrow_forwardThe structure shown here is best described as a(n) CH3 H H₂N -OH H3C CH3 O zwitterion O dipeptide O tripeptide Otetrapeptide O amino acid at neutral pH ZI U=O IZ I =O H HH OHarrow_forwardA novel new method of peptide synthesis involves formation of an amide bond by reaction of an a-keto acid with an N-alkylhydroxylamine. OH + CO2 + H20 CO2 TR' Draw curved arrows to show the movement of electrons in the following step of the reaction mechanism Arrow-pushing Instructions :0: :ö: c-ö: -R' .R' H20 CO2 A R R H-Aarrow_forward
- A3arrow_forwardName the peptide below using their single-letter labels (example: HCFAR) NH₂ OH Glycine (Gly; G) HO 0 H NH₂ Serine (Ser; S) NH OH NH₂ Methionine (Met; M) H₂N N Me HS OH HO NH₂ NH₂ Alanine (Ala; A) OH NH₂ Cysteine (Cys; C) my OH OH OH NH₂ Threonine (Thr; T) H₂N HOH OH NH₂ Valine (Val, V) H₂N. HN HN H₂N OF NH₂ Histidine (His; H) NH₂ OH OH Glutamine (Gln; Q) OH NH₂ NH₂ NH₂ Leucine (Leu; L) H OH OH HO OH HO O NH₂ Aspartic acid (Asp; D) NH₂ Phenylalanine (Phe; F) HN NH₂ Glutamic acid (Glu; E) OH H₂N NH₂ OH OH OH H₂N HO ΝΗ Proline (Pro ; P) H Lysine (Lys; K) NH₂ OH OH Hy NH₂ Asparagine (Asn ; N) OH NH₂ OHarrow_forwardGlycine is a diprotic acid, which can potentially undergo two dissociation reactions, one for the a-amino group (-NH3), and the other for the carboxyl (-COOH) group. Therefore, it has two pKą values. The carboxyl group has a pK₁ of 2.34 and the a-amino group has a pK₂ of 9.60. Glycine can exist in fully deprotonated (NH₂-CH₂-COO-), fully protonated (NH3-CH₂-COOH), or zwitterionic form (NH3-CH₂-COO-). Match the pH values with the corresponding form of glycine that would be present in the highest concentration in a solution of th pH. fully deprotonated form NH,−CH,−COO- pH 11.9 pH 6.0 pH 8.0 fully protonated form NH3-CH₂-COOH pH 1.0 Answer Bank pH 7.0 zwitterionic form NH3-CH₂-COO-arrow_forward
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