All amino acids have two ionizable functional groups: an a-amino group (average pK, of 9.4) and an a-carboxylic acid group (average pKą of 2.2). Tyrosine also has an ionizable side chain (R group) with a pKą of about 10.1. One of the possible ionization states of tyrosine is shown. HaN — CH -C —он CH2 OH At what pH would the structure be the predominant ionization state? Consider the ionization state of all three of the

All amino acids have two ionizable functional groups: an a-amino group (average pK, of 9.4) and an a-carboxylic acid group (average pKą of 2.2). Tyrosine also has an ionizable side chain (R group) with a pKą of about 10.1. One of the possible ionization states of tyrosine is shown. HaN — CH -C —он CH2 OH At what pH would the structure be the predominant ionization state? Consider the ionization state of all three of the

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter3: Stereoisomerism And Chirality

Section3.8: The Significance Of Chirality In The Biological World

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22-61 Polyglutamic acid (a polypeptide chain made only of glutamic acid residues) has an a-helix conformation below pH 6.0 and a random-coil conformation above pH 6.0. What is the reason for this conformational change?
All amino acids have two ionizable functional groups: an a-amino group (average pK, of 9.4) and an a-carboxylic acid group (average pK, of 2.2). Tyrosine also has an ionizable side chain (R group) with a pK, of about 10.1. One of the possible ionization states of tyrosine is shown. H3N-CH -C-OH CH2 ÓH At what pH would the structure be the predominant ionization state? Consider the ionization state of all three of the functional groups. The protonated form of the R group of tyrosine is shown in the structure. The ratio of the protonated form to the charged (deprotonated) form depends on the pK, of the R group and the pH of the solution. Select the pH value at which the charged form of the R group would predominate.
Glycine 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-
Para-aminobenzoic acid has two ionizable groups. One is a carboxylic acid that ionizes through loss of a proton thereby forming a charged para-aminobenzoic acid carboxylate anion, and the other is an amine connected to an aromatic (benzene) ring that ionizes by accepting an H+ to form a positively charged ammonium ion. The pk of the carboxylic acid is 4.9 and the pk of the amino group is 2.5. Assume that the intracellular pH within a bacterial cell is 7.0. N- H O-H H + H-N- H pK₂ = 2.5 Which of the following structures correctly depicts how most of the para-aminobenzoic acid is ionized at pH 7? A. B. O-H C. H H + H-N- H H D. H N- O-H H pK₂ = 4.9
All amino acids have two ionizable functional groups: an a-amino group (average pK, of 9.4) and an a-carboxylic acid group (average pK, of 2.2). Lysine also has an ionizable side chain (R group) with a pK, of about 10.5. One of the possible ionization states of lysine is shown in the image. i H₂N-CH-C-OH CH₂ 1 Incorrect CH₂ CH₂ CH₂ NH₂ At what pH would the structure be the predominant ionization state? Consider the ionization state of all three of the functional groups. Show Transcribed Text 11.9 S The protonated form of the R group of lysine is shown in the structure. The ratio of the charged (protonated) form to the deprotonated form depends on the pK, of the R group and the pH of the solution. 12.0 10.5 5.4 Select all the pH values at which the charged form of the R group would predominate. 2.2
All amino acids have two ionizable functional groups: an a-amino group (average pK, of 9.4) and an a-carboxylic acid group (average pK, of 2.2). Glutamic acid has an ionizable side chain (R group) with a pK, of about 4.1. One of the possible ionization states of glutamic acid is shown in the image. H₂N-CH-C-OH CH₂ At what pH would this structure of glutamic acid be the predominant ionization state? Consider the ionization state of all three of the functional groups. OH The protonated form of the R group of glutamic acid is shown in the structure. The ratio of the protonated form to the charged (deprotonated) form depends on the pK, of the R group and the pH of the solution. 2.6 4.1 1.5 Select the pH values at which the charged form of the R group would predominate. 7.0 11.3
All amino acids have two ionizable functional groups: an α‑amino group (average p?a of 9.4) and an α‑carboxylic acid group (average p?a of 2.2). Aspartic acid has an ionizable side chain (R group) with a p?a of about 3.8. One of the possible ionization states of aspartic acid is shown in the image. The protonated form of the R group of aspartic acid is shown in the structure. The ratio of the protonated form to the charged (deprotonated) form depends on the p?a of the R group and the pH of the solution. Select all the pH values at which the charged form of the R group would predominate.
Choose the structure that best represents the following amino acid at pH = 2. О А O NH3 A ОН ISO NH₂ В ОН NH₂ ОН NH₂ с OH NH3 А D
TRUE OR FALSE: Naturally-occurring amino acids have the L- configuration. All amino acids are chiral except for Proline. Leucine has more than one chiral carbon in their structures. Peptide bonds are amide bonds formed from the reaction of the a-carboxyl group of one amino acid and the a-amino group of another amino acid. Lysine is considered a basic amino acid because of the presence of the amino group at the a- carbon. [Choose ] [Choose ] TRUE FALSE [Choose ] [Choose ] [Choose]
Shown below is the amino acid tyrosine in its protonated state, with the pK₂of each ionizable proton indicated. pK₂ = 10 HO COOH pk = 9 pK₂ = 2 Which best represents the predominant state of tyrosine at pH 7? a HO. O O OO a b U H3N P H₂N COOH b H₂N COO с НО. H₂N COO d HO. H₂N COO
Ammonium group are m- directing but amino groups are o,p-directing. * O True O False All of the following C6H6 compounds has a single set of structurally equivalent hydrogen atoms. * H-CEC-C-C-CEC-H H2 H2 I II III IV VI O True O False
Ornithine is an amino acid that is not used in the synthesis of proteins, but is an important intermediate in several metabloic pathways including the urea cycle and the synthesis of polyamines. It has a perfectly ordinary terminal amino group and terminal carboxyl group like any other amino acid (so use the pKas for those groups given on your amino acids handout), and a side chain with a single ionizable side group with a pKa of 10.3. If ornithine is placed in solution at pH 7.0, it has a net charge of +1. What would the net charge on this amino acid be if the pH of the solution was raised to pH 12.0? Please explain your reasoning.