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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.
The current production method is based on the first scalable synthesis developed by Gilead Sciences [4] starting from naturally occurring quinic acid or shikimic acid.Due to lower yields and the extra steps required (because of the additional dehydration), the quinic acid route was dropped in favour of the one based on shikimic acid, which received further improvements by Hoffmann-La Roche.
Oseltamivir, sold under the brand name Tamiflu among others, is an antiviral medication used to treat and prevent influenza A and influenza B, viruses that cause the flu. [5] Many medical organizations recommend it in people who have complications or are at high risk of complications within 48 hours of first symptoms of infection. [ 6 ]
[10] [11] [12] An industrial method for the production of shikimic acid using fermentation of E. coli bacteria was discovered in 2005, [13] [14] and applied in the 2009 swine flu pandemic to address Tamiflu shortages, eventually reversing price increases for star anise as a raw material of shikimic acid. [15]
The shikimate pathway (shikimic acid pathway) is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids (tryptophan, phenylalanine, and tyrosine). This pathway is not found in mammals.
Aminoshikimic acid is an unnatural carbohydrate, although aminoshikimic acid is the namesake of the aminoshikimate pathway, which generates the 3-amino-5-hydroxybenzoic acid (AHBA) starter unit required for the biosynthesis of the ansamycins and mitomycins. [1]
Intraosseous infusion (IO) is the process of injecting medication, fluids, or blood products directly into the bone marrow; [1] this provides a non-collapsible entry point into the systemic venous system. [2]
Dactylifric acid (also known as dattelic acid or 5-O-caffeoylshikimic acid [2] [3] [4]) is an ester derived from caffeic acid and shikimic acid. It and its isomers are enzymic browning substrates found in dates (Phoenix dactylifera fruits). [3] [5] Some older sources identify dactylifric acid as 3-O-caffeoylshikimic acid. [5]
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