Organic Chemistry - Camphor Synthesis

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SUMMARY

The discussion focuses on the biosynthesis of camphor from acetyl-CoA and acetic acid, specifically within a biological context. The process involves the phosphorylation of Co-A by two moles of ATP, creating a leaving group that facilitates the formation of a bicyclic structure. Carbon-13 labeled acetic acid, derived from Carbon-13 enriched CO2 and CH3MgBr, is utilized in the synthesis, with the plant Cinnamomum camphora being the biological source for camphor isolation. The inquiry also addresses whether the bicyclic bridge in camphor incorporates the C-13 enriched carbon.

PREREQUISITES
  • Understanding of biosynthetic pathways in organic chemistry
  • Knowledge of acetyl-CoA metabolism
  • Familiarity with isotopic labeling techniques in organic synthesis
  • Basic principles of ATP phosphorylation and its role in biochemical reactions
NEXT STEPS
  • Research the biosynthetic pathway of terpenes, focusing on monoterpenes like camphor
  • Study the role of ATP in biochemical phosphorylation reactions
  • Explore isotopic labeling methods in organic synthesis and their applications
  • Investigate the metabolic capabilities of Cinnamomum camphora in camphor production
USEFUL FOR

Chemists, biochemists, and students interested in organic synthesis, particularly those focusing on natural product biosynthesis and metabolic pathways.

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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.
 
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Try out this link

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