Shikimic acid

Shikimic Acid is a key biochemical metabolite that plays a central role in the biosynthesis of many aromatic compounds in both plants and microorganisms. It is a white crystalline compound of non-nitrogenous acid found in various plants. Shikimic acid is an important precursor in the pharmaceutical industry, particularly in the synthesis of the antiviral drug oseltamivir (Tamiflu), which is used in the treatment of influenza.

Overview

Shikimic acid derives its name from the Japanese flower Shikimi (Illicium anisatum), from which it was first isolated. The compound is a cyclohexene, a six-membered ring containing five carbons and one oxygen atom, with three hydroxyl (-OH) groups attached, making it a trihydroxy cyclohexene. Its chemical formula is C7H10O5. Shikimic acid is not found in animals; instead, animals must obtain aromatic amino acids from their diet, which are metabolized from shikimic acid in plants and microorganisms.

Biosynthesis

The biosynthesis of shikimic acid is a critical process in the shikimate pathway, which is responsible for the production of phenylalanine, tyrosine, and tryptophan. These aromatic amino acids are precursors to a wide range of secondary metabolites, including alkaloids, flavonoids, and lignins. The shikimate pathway involves seven enzymatic steps, starting from the condensation of phosphoenolpyruvate and erythrose-4-phosphate to eventually form shikimic acid.

Applications

Shikimic acid serves as a starting material in the synthesis of numerous pharmaceuticals, most notably oseltamivir (Tamiflu), an antiviral medication used to combat influenza. The demand for shikimic acid surged during the H1N1 influenza pandemic, highlighting its importance in antiviral therapy. Additionally, shikimic acid is used in the synthesis of other drugs, including anti-cancer, anti-thrombotic, and anti-inflammatory agents.

Sources

While shikimic acid is present in many plants, significant commercial sources include the star anise (Illicium verum), from which it is extracted as a primary source for pharmaceutical synthesis. Other sources include the ginkgo tree (Ginkgo biloba) and the sweetgum (Liquidambar styraciflua). Advances in biotechnology have led to the development of genetically modified microorganisms capable of producing shikimic acid, offering a sustainable alternative to plant extraction.

Challenges and Future Directions

The reliance on plant sources for shikimic acid poses challenges related to supply stability and environmental sustainability. Seasonal variations, crop diseases, and geopolitical factors can affect the availability and price of shikimic acid. Biotechnological advancements, including metabolic engineering and synthetic biology, are being explored to enhance the microbial production of shikimic acid, aiming to provide a more reliable and environmentally friendly production method.

Conclusion

Shikimic acid is a vital biochemical compound with significant implications in the pharmaceutical industry. Its role as a precursor in the synthesis of various drugs, including antivirals, underscores the importance of understanding its biosynthesis, sources, and applications. Continued research and development in biotechnological production methods are essential to meet the global demand for shikimic acid and its derivatives.

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Shikimic acid gallery

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  Shikimate pathway 1

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  Shikimate pathway 2