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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sharbeldam on February 26, 2020, 02:16:24 PM

Title: How does the liver does this mechanism wise?
Post by: sharbeldam on February 26, 2020, 02:16:24 PM

What is the mechanism of this reaction ( metabolism of a drug )

Thanks for help

I would have put my try but I honestly have no idea how the liver does this for the drug. it converted a single bond to enol.

Title: Re: How does the liver does this mechanism wise?
Post by: Babcock_Hall on February 26, 2020, 04:19:35 PM

As you know, it is up to you to share you thoughts before we can help you.  I will try to give you a start.  How would you classify the reaction that you have drawn (meaning is it an isomerization, reduction, etc.)?  What liver enzymes do you know that are involved with xenobiotics?

Title: Re: How does the liver does this mechanism wise?
Post by: AWK on February 26, 2020, 04:21:14 PM

It is probably enzymatic oxidation by one of from cytochrome P450 family.

Title: Re: How does the liver does this mechanism wise?
Post by: sharbeldam on February 26, 2020, 06:45:54 PM

I might be of a beginner level, I know it's enzymatic but the oxidation that I know in chemical synthesis do not usually transform single bond to enol, is there a mechanism  ( a specific reaction that we learn in O-chem ) that explains how an enzyme does this?

Title: Re: How does the liver does this mechanism wise?
Post by: AWK on February 26, 2020, 06:50:49 PM

Enzymic reactions are always stepwise.

Title: Re: How does the liver does this mechanism wise?
Post by: sharbeldam on February 27, 2020, 04:52:25 AM

is it possible to figure out the exact mechanism of the liver oxidation of this specific drug? or are you saying its too many steps ?

Title: Re: How does the liver does this mechanism wise?
Post by: AWK on February 27, 2020, 05:41:29 AM

From a chemical point of view, there are several stages. But from the biochemical point of view these stages are more because the energy consumed or given away in biological systems is transferred in small portions - less than 40 kJ / mol. Read yourself about cytochrome oxidase, ATP and NAD/NADH.

Think as a chemist and sketch a few step mechanism.

Title: Re: How does the liver does this mechanism wise?
Post by: sharbeldam on February 27, 2020, 06:55:16 AM

Any link you have that helps me read about their reactions? I looked it up and found nothing regarding my reaction's transformations.

Appreciate the help

Title: Re: How does the liver does this mechanism wise?
Post by: rolnor on February 27, 2020, 07:06:10 AM

https://sv.wikipedia.org/wiki/Cytokrom_P450

Title: Re: How does the liver does this mechanism wise?
Post by: sharbeldam on February 27, 2020, 07:37:32 AM

One reaction must be the aliphatic hydroxlation which i found the mechanism for, but I wonder why exactly this carbon undergoes it.
Im still trying to figure out how the single bond becomes an alkene after the hydroxylation.

Title: Re: How does the liver does this mechanism wise?
Post by: AWK on February 27, 2020, 07:49:49 AM

Oxidation of alcohol

Title: Re: How does the liver does this mechanism wise?
Post by: rolnor on February 27, 2020, 07:57:50 AM

You first get the alcohol, then ketone and this in turn forms a enolform.

Title: Re: How does the liver does this mechanism wise?
Post by: sharbeldam on February 27, 2020, 08:01:31 AM

I truly appreciate the help guys, I hope that you realize how important you are to the community.

Title: Re: How does the liver does this mechanism wise?
Post by: Babcock_Hall on February 27, 2020, 01:19:52 PM

@OP, Can you think of any enzymes that oxidize alcohols?  What are the possible cosubstrates?