Methylation of glucose (mechanism)

In summary, the conversation is about the confusion regarding the type of substitution reaction that is taking place in a specific chemical reaction involving glucose and ICH3. The person is wondering why it is considered a nucleophile substitution instead of an electrophile substitution, and is seeking clarification on their thought process. The expert explains that in organic chemistry, reactions are typically viewed as occurring at the carbon substrate, so the reaction can be seen as either an electrophilic substitution of H by methyl at the O of glucose, or a nucleophilic substitution at the C of CH3I.
  • #1
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Homework Statement
Nucleophilic or electrophilic substitution
Relevant Equations
x
Hi,
I don't understand why this correction would be a nucleophile substitution?
From what understand : The O atoms in the cyclic glucose acts as nucleophiles. ICH3 is also a nucleophile due to the presence of iodine's "non bonding electron pairs" (sorry I don't know the right term for this), and since I is a halogen, CH3 bares partial positive charge.
Ch3 being electrophilic, comes and replace H. So why isn't it a electrophile substitution?
Can you please explain to me what went wrong in my thought process?
And do you have a way that which I can determine what kind of substitution it is everytime because I don't really know which molecule would be the one that that has a substituted group? Like from this case, is H substituted by CH3 or I substituted by glucose?
Thank you so much for your help!
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  • #2
In a sense it's all the same, because you can't have nucleophiles without electrophiles, just as you can't have acid without base, or oxidation without reduction. But in organic chemistry, we think of the reaction occurring at the carbon substrate. Thus, while the above reaction could be seen as an electrophilic substitution of H by methyl at the O of glucose, it would be normal to think of it as a nucleophilic substitution at the C of CH3I.
 
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Likes duchuy
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thank you sir!
 

1. What is methylation of glucose?

Methylation of glucose is a chemical process in which a methyl group (-CH3) is added to a glucose molecule. This process involves the transfer of a methyl group from one molecule to another, resulting in the formation of a new molecule.

2. Why is methylation of glucose important?

Methylation of glucose is important because it plays a crucial role in many biological processes. It is involved in the regulation of gene expression, cellular signaling, and metabolism. It also helps in the formation of important molecules such as DNA and proteins.

3. What is the mechanism of methylation of glucose?

The mechanism of methylation of glucose involves the transfer of a methyl group from a methyl donor molecule, such as S-adenosylmethionine (SAM), to the hydroxyl group (-OH) of glucose. This process is catalyzed by enzymes called methyltransferases.

4. How does methylation of glucose affect gene expression?

Methylation of glucose can affect gene expression by altering the structure and function of DNA. Methylation of specific regions of DNA can turn genes "on" or "off", regulating their expression. This can have a significant impact on cellular processes and can also be involved in the development of diseases.

5. Can methylation of glucose be reversed?

Yes, methylation of glucose can be reversed through a process called demethylation. This involves the removal of the methyl group from the glucose molecule, which can be done by specific enzymes. Demethylation is important for maintaining proper gene expression and cellular function.

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