Organic Chemistry - Camphor Synthesis

[DDS]

Hello guys and girls. I am writing to you all today in hopes that someone out there will be able to help me with my problem. I am asked to synthesize the molecule camphor starting merely from acetly-CoA and Acetic Acid. This must be done in a biological manner. Ie. The Co-A group will be phosporylated by two moles of ATP giving you a fanastic leaving group (OPP) which then can leave the join the linear molecule into its bicylco podcut.

Here is the question in full.

Outline all of the steps involved in the biosynthesis of the monterpene camphor from acetyl-CoA. Carbon 13 labeled acetic acid was prepared from Carbob 13 enriched CO2 and normal CH3MgBr. This acetic acid was then fed to the plant Cinnamomum camphora and camphor was isolated a few days later. Outline the biosynthesis and state wheter or not the bicylcobridge in camphor contains the C13 enriched Carbon or not.

Now for what i know; i know you can synthesize cmaphor easily from only two molecules of Isoprenes. However, in this scenario since it is asking for a biological perspective i am not sure if the body is capable of riping of an acidic hydrogen like LDA would and then forming a B-keto acid with the attached Co-A portion.

Any help would be extremely helpfull.

 

[GCT]

Try out this link

http://www.iisc.ernet.in/academy/resonance/Oct1996/pdf/Oct1996p37-43.pdf

 

[Blueshift5]

Dear writer,

Thank you for reaching out for help with your organic chemistry problem. The synthesis of camphor from acetyl-CoA and acetic acid is a fascinating topic in biosynthesis. I am happy to provide some steps and insights that may help you in your assignment.

First, let's start with the biosynthesis of camphor from acetyl-CoA. Acetyl-CoA is a common intermediate in many metabolic pathways and can be derived from various sources such as glucose, fatty acids, and amino acids. In the case of camphor synthesis, acetyl-CoA is derived from fatty acid synthesis.

The first step in the biosynthesis of camphor is the phosphorylation of acetyl-CoA by two moles of ATP, as you mentioned. This results in the formation of acetyl phosphate, which is a fantastic leaving group with a high energy phosphate bond. The next step is the condensation of acetyl phosphate with another molecule of acetyl-CoA to form acetoacetyl-CoA. This reaction is catalyzed by the enzyme acetoacetyl-CoA thiolase.

Next, the acetoacetyl-CoA undergoes a series of reactions known as the mevalonate pathway, which converts it into isopentenyl pyrophosphate (IPP). This pathway involves several enzymes and intermediates and results in the formation of IPP, which is a five-carbon building block for terpenes.

In the final step, two molecules of IPP are condensed to form geranyl pyrophosphate (GPP), which contains 10 carbons. GPP is then converted into farnesyl pyrophosphate (FPP), which contains 15 carbons. Finally, FPP is converted into camphor through a series of cyclization and oxidation reactions.

Now, let's address the question of whether the bicylcobridge in camphor contains the C13 enriched carbon or not. As you mentioned, carbon-13 labeled acetic acid was used in the synthesis, which means that any carbon atoms derived from that acetic acid will also be labeled. Therefore, the bicylcobridge in camphor will contain the C13 enriched carbon.

I hope this explanation helps you in your assignment. Keep in mind that this is a simplified version of the biosynthesis of camphor, and there may be other enzymes and intermediates involved in the process. However, the main steps and reactions remain the same