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Shikimic acid can also be extracted from the seeds of the sweetgum (Liquidambar styraciflua) fruit, [2] which is abundant in North America, in yields of around 1.5%. For example, 4 kg (8.8 lb) of sweetgum seeds is needed for fourteen packages of Tamiflu. By comparison, star anise has been reported to yield 3% to 7% shikimic acid.
Synthesis of Tamiflu. The synthesis commences from naturally available (−)-shikimic acid. The 3,4-pentylidene acetal mesylate is prepared in three steps: esterification with ethanol and thionyl chloride; ketalization with p-toluenesulfonic acid and 3-pentanone; and mesylation with triethylamine and methanesulfonyl chloride.
Oseltamivir was discovered by scientists at Gilead Sciences using shikimic acid as a starting point for synthesis; shikimic acid was originally available only as an extract of Chinese star anise; but by 2006, 30% of the supply was manufactured recombinantly in E. coli. [65] [66] Gilead exclusively licensed their relevant patents to Roche in ...
Star anise oil is a highly fragrant oil used in cooking, perfumery, soaps, toothpastes, mouthwashes, and skin creams. Until 2012, when they switched to using genetically modified E. coli, Roche Pharmaceuticals used up to 90% of the world's annual star anise crop to produce oseltamivir (Tamiflu) via shikimic acid. [3]
Aminoshikimic acid is an intriguing alternative to shikimic acid as a starting material for the synthesis of neuraminidase inhibitors such as the antiinfluenza agent oseltamivir. [3] Aminoshikimic acid is also a versatile chiral starting material for the synthesis of new pharmaceuticals.
Neuraminidase inhibitors (NAIs) are a class of drugs which block the neuraminidase enzyme. They are a commonly used antiviral drug type against influenza. Viral neuraminidases are essential for influenza reproduction, facilitating viral budding from the host cell.
Dr. Norbert Bischofberger (born 10 January 1956 in Mellau, Austria) is an Austrian scientist and one of the inventors of the antiviral drug Tamiflu generically known as oseltamivir, which is, as of 2009, the only oral medication on the market to treat influenza A and B as well as the 2009 Pandemic H1N1 (), the spread of which caused an ongoing pandemic in 2009. [1]
It is the major source of the chemical compound shikimic acid, a primary precursor in the pharmaceutical synthesis of anti-influenza drug oseltamivir (Tamiflu). [93] Inula helenium: Elecampane: It is used in herbal medicine as an expectorant and for water retention. [94]
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