Draw the predominant form of Gly-Gly when 2.0 moles of OH- is added.
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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Transcribed Image Text:**Question: Draw the predominant form of Gly-Gly when 2.0 moles of OH⁻ is added.**
In this exercise, you are asked to determine and draw the predominant form of the dipeptide Glycylglycine (Gly-Gly) upon addition of 2.0 moles of hydroxide ions (OH⁻).
To solve this problem, one must consider the chemical structure of Gly-Gly and the effect of adding hydroxide ions. Hydroxide ions will likely deprotonate the amino and carboxyl groups in the peptide sequence.
- **Gly-Gly Structure:**
- Glycine (Gly) has the side chain -H.
- In dipeptide form, two glycine molecules are linked by a peptide bond (CONH).
The addition of OH⁻ typically results in the deprotonation of acidic protons:
1. Carboxyl (-COOH) group deprotonation leading to -COO⁻.
2. Amino (-NH₃⁺) deprotonation leading to -NH₂.
Since 2.0 moles of OH⁻ are added, this sufficient quantity will fully deprotonate the available acidic protons in Gly-Gly.
**Detailed Steps to Draw the Predominant Form:**
1. Begin with the Gly-Gly structure:
```
NH3⁺-CH2-CO-NH-CH2-COOH
```
2. Identify the groups that can be deprotonated by OH⁻ action:
- The NH3⁺ group can lose a proton to become NH2.
- The COOH group can lose a proton to become COO⁻.
3. Upon addition of 2.0 moles of OH⁻, proton distribution will lead to:
```
NH2-CH2-CO-NH-CH2-COO⁻
```
So, the predominant form should be represented as the structure provided above. This analysis helps understand the biochemical interactions in a basic environment where Gly-Gly is adjusted with a strong base like OH⁻.
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