EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
Author: SMITH
Publisher: MCGRAW-HILL HIGHER EDUCATION
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Textbook Question
Chapter 27, Problem 37P
a. Draw the structure of the tripeptide A–A–A, and label the two ionizable
b. What is the predominant form of A–A–A at
c. The pKa values for the two ionizable functional groups (3.39 and 8.03) differ considerably from the pKa values of alanine (2.35 and 9.87; see Table 29.1). Account for the observed pKa differences.
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Students have asked these similar questions
A. Write the structure of the pentapeptide GLDSC.
B. What is the complete name of this pentapeptide?
Show a tertiary structure of ACGGC after a
disulfide bond forms.
A sample of an unknown peptide was divided into
two aliquots. One aliquot was treated with trypsin;
the other was treated with cyanogen bromide.
Given the following sequences (N-terminal to C-
terminal) of the resulting fragments, deduce the
sequence of the original peptide.
Trypsin treatment
Asn-Thr-Trp-Met-lle-Lys
Gly-Tyr-Met-Gin-Phe
Val-Leu-Gly-Met-Ser-Arg
Cyanogen bromide treatment
Gin-Phe
Val-Leu-Gly-Met
lle-Lys-Gly-Tyr-Met
Ser-Arg-Asn-Thr-Trp-Met
Of the 20 protein-derived amino acids shown in Table 27.1, how many contain
Q.) sulfur?
Which of the following clarifications is false?
Select one:
to.
fibroin contains AA with sparse side chains
b.
disulfide bridges play an important role in
maintaining alpha keratin structures.
C.
fibroin is a protein in which polypeptide
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d.
Gly residues are abundant in collagen
е.
collagen is a protein in which polypeptides
are in the alpha helix conformation
Chapter 27 Solutions
EBK ORGANIC CHEMISTRY
Ch. 27.1 - Prob. 1PCh. 27.1 - Problem 29.2
What form exists at the isoelectric...Ch. 27.1 - Problem 29.3
Explain why the of the group of an...Ch. 27.1 - Prob. 4PCh. 27.2 - Problem 29.5
What -halo carbonyl compound is...Ch. 27.2 - Problem 29.6
The enolate derived from diethyl...Ch. 27.2 - Problem 29.7
What amino acid is formed when is...Ch. 27.2 - Problem 29.8
What aldehyde is needed to synthesize...Ch. 27.2 - Problem 29.9
Draw the products of each...Ch. 27.3 - Prob. 10P
Ch. 27.3 - Prob. 11PCh. 27.3 - Prob. 12PCh. 27.4 - Problem 29.13
What alkene is needed to synthesize...Ch. 27.5 - Problem 29.14
Draw the structure of each peptide....Ch. 27.5 - Problem 29.15
Name each peptide using both the...Ch. 27 - Draw the product formed when the following amino...Ch. 27 - With reference to the following peptide: a...Ch. 27 - Prob. 31PCh. 27 - Histidine is classified as a basic amino acid...Ch. 27 - Tryptophan is not classified as a basic amino acid...Ch. 27 - What is the structure of each amino acid at its...Ch. 27 - What is the predominant form of each of the...Ch. 27 - 29.37 What is the predominant form of each of the...Ch. 27 - a. Draw the structure of the tripeptide A–A–A, and...Ch. 27 - 29.39 Draw the organic products formed in each...Ch. 27 - 29.40 What alkyl halide is needed to synthesize...Ch. 27 - Prob. 50PCh. 27 - Draw the structure for each peptide: (a) Phe–Ala;...Ch. 27 - 29.52 For the tetrapeptide Asp–Arg–Val–Tyr:
a....Ch. 27 - Prob. 53PCh. 27 - Prob. 54PCh. 27 - 29.55 Draw the amino acids and peptide fragments...Ch. 27 - Prob. 56PCh. 27 - Prob. 57PCh. 27 - Prob. 58PCh. 27 - 29.59 An octapeptide contains the following amino...Ch. 27 - 29.60 Draw the organic products formed in each...Ch. 27 - 29.65 Draw the mechanism for the reaction that...Ch. 27 - 29.66 Which of the following amino acids are...Ch. 27 - 29.67 After the peptide chain of collagen has been...Ch. 27 - Prob. 68PCh. 27 - Prob. 69PCh. 27 - 29.70 The anti-obesity drug orlistat works by...Ch. 27 - Prob. 71P
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 10. Which side chain would most likely be found in the interior of a protein, away from the aqueous environment? a. -CH2OH b. -CH2SH с. -СH-CООН d. -CH2CONH2 e.arrow_forwardOf the 20 protein-derived amino acids shown in Table 27.1, which contain Q.) two chiral centersarrow_forwardPlease explain step by step procedure of the final primary structure. Thank you!arrow_forward
- Identify the name of the amino acid and classify it based on: a. chirality b. configuration c. r-group (side chain) d. acidic-basic property e. polarity f. essentialityarrow_forward1. Draw the tetrapeptide DASK and estimate the pl. What is the approximate net charge on the peptide at pH 2, pH 7, and pH 12?arrow_forward1A) Draw a peptide solely derived from L- amino acids. 1B) Note all stereocenters and assign R,S configuration 1C) How many stereoisomers are possible for your peptide if both L- and D-amino acids were randomly incorporatedarrow_forward
- 1. a) Classify the amino acids according to the nature of their side chains (R groups), stating which are polar, non-polar, acidic and basic. Draw the structure of the amino acid glutamic acid in neutral solution at pH7.0. b) What is meant by the term isoelectric point of an amino acid? Discuss how is it related to the pKa values of an amino acid? c) What practical technique would you use to separate a mixture of the amino acids arginine, valine and glutamic acid? State briefly how it works. d) Describe in detail the two analytical methods that can be used to separate a complex mixture of proteins, yielding individual proteins with different amino acid sequences. Many thanks.arrow_forward5. A peptide is synthesized using a solid-phase peptide synthesis strategy. Amino acids are typically protected using a Boc group, Fmoc group or Cbz group. Which amino acids will require two protecting groups instead of one? A. E В. G С. L D. W E. F nswer: Explanation: 34%arrow_forwardTaking the structure of the amino acids into account, give a comparative discussion of these pK values : Alanine : 2.34 : 6.1 : 9.70 Histidine: 1.82 : 9.17arrow_forward
- 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? C. What is the pH of D at its isoelectric point? D. Show the structure of this amino acid at its isoelectric point. E. What is the charge of this amino acid in a strongly acidic solution?arrow_forwardb) The methyl group at the C terminus of aspartame can be cleaved by concentrated sulfuric acid (conc. H₂SO4) to reveal the carboxylic acid (compound 1), which has a pK₂ of 2.43. OH NH₂ OCH3 conc. H₂SO4 OH NH₂ OH Compound 1 The other two pKa values in the molecule are unchanged. It is useful to calculate the isoelectric point (pl) when planning to separate charged species from neutral species with electrophoresis. pKal + PK₂2 2 pl = HINT: i) Calculate the isoelectric point of aspartame. ii) Calculate the isoelectric point of compound 1 and explain your reasoning behind the calculation.arrow_forwardAnother method to form a peptide bond involves a two-step process Conversion of a Boc-protected amino acid to a p-nitrophenyl ester. Why does a p-nitrophenyl ester “activate” the carboxy group of thefirst amino acid to amide formation?arrow_forward
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