Q4. The estimated gKa of hydroimidazolone's R group is 6.93. If the pK₁ (a-COOH) and pK₂ (a-NH₂) of hydroimidazolone remain unchanged from its parent amino acid, would the pl, of hydroimidazolone be higher (more basic) or lower (more acidic) than that of arginine? Explain your reasoning.
Q4. The estimated gKa of hydroimidazolone's R group is 6.93. If the pK₁ (a-COOH) and pK₂ (a-NH₂) of hydroimidazolone remain unchanged from its parent amino acid, would the pl, of hydroimidazolone be higher (more basic) or lower (more acidic) than that of arginine? Explain your reasoning.
Biochemistry
9th Edition
ISBN:9781319114671
Author:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Publisher:Lubert Stryer, Jeremy M. Berg, John L. Tymoczko, Gregory J. Gatto Jr.
Chapter1: Biochemistry: An Evolving Science
Section: Chapter Questions
Problem 1P
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![Q4. The estimated pKa of hydroimidazolone's R group is 6.93. If the pK₁ (a-COOH) and pK2 (a-NH₂) of
hydroimidazolone remain unchanged from its parent amino acid, would the pl, of hydroimidazolone be higher
(more basic) or lower (more acidic) than that of arginine? Explain your reasoning.
Accumulation of macromolecules chemically modified by the addition of MGO has been associated with many
age-related diseases, including cancer. Thankfully, mammalian cells have developed several enzymatic
mechanisms to clear cytotoxic MGO from the cell. The principal detoxifying pathway found in the cytosol of all
cells is the Glyoxalase (Glo) system, shown in figure 3 below. Using glutathione as a co-substrate, this
pathway converts MGO to D-lactate which can ultimately be metabolized in peroxisomes.
CH₂
+
je sysh
H CH₂SH
Methylglyoxal
(MC)
Glo3
GSH +
H₂O
HO
NH₂,
D-Lactate
CH₂ Clo2
y-Glutamyl-L-cysteinylglycine
(GSH)
-
GS
H₂O
HO
CH₂
Non-enzymatic
GS
HO-
gl
CH₂
Hemithioacetal
Glo1
OH
[[X=X]
CH₂
GS
Enediol(ate) enzyme intermediates 1
CH₂
S-D-Lactoylglutathione
Figure 3-Reaction schemes for the glyoxalase enzymes. Image source: Honek, John F. "Glyoxalase biochemistry"
Biomolecular Concepts, 2015 6(5-6), p. 401-414.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Faa3c8bce-9ac3-44bc-8e19-753f7b8befa4%2Ff9c7bce7-b8e7-4034-b7a8-0a345476e33d%2F425wpl_processed.jpeg&w=3840&q=75)
Transcribed Image Text:Q4. The estimated pKa of hydroimidazolone's R group is 6.93. If the pK₁ (a-COOH) and pK2 (a-NH₂) of
hydroimidazolone remain unchanged from its parent amino acid, would the pl, of hydroimidazolone be higher
(more basic) or lower (more acidic) than that of arginine? Explain your reasoning.
Accumulation of macromolecules chemically modified by the addition of MGO has been associated with many
age-related diseases, including cancer. Thankfully, mammalian cells have developed several enzymatic
mechanisms to clear cytotoxic MGO from the cell. The principal detoxifying pathway found in the cytosol of all
cells is the Glyoxalase (Glo) system, shown in figure 3 below. Using glutathione as a co-substrate, this
pathway converts MGO to D-lactate which can ultimately be metabolized in peroxisomes.
CH₂
+
je sysh
H CH₂SH
Methylglyoxal
(MC)
Glo3
GSH +
H₂O
HO
NH₂,
D-Lactate
CH₂ Clo2
y-Glutamyl-L-cysteinylglycine
(GSH)
-
GS
H₂O
HO
CH₂
Non-enzymatic
GS
HO-
gl
CH₂
Hemithioacetal
Glo1
OH
[[X=X]
CH₂
GS
Enediol(ate) enzyme intermediates 1
CH₂
S-D-Lactoylglutathione
Figure 3-Reaction schemes for the glyoxalase enzymes. Image source: Honek, John F. "Glyoxalase biochemistry"
Biomolecular Concepts, 2015 6(5-6), p. 401-414.
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