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The low isolation yield of shikimic acid from the Chinese star anise is blamed for the 2005 shortage of oseltamivir. 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 ...
The pathway starts with two substrates, phosphoenol pyruvate and erythrose-4-phosphate, and ends with chorismate (chrorismic acid), a substrate for the three aromatic amino acids. The fifth enzyme involved is the shikimate kinase , an enzyme that catalyzes the ATP -dependent phosphorylation of shikimate to form shikimate 3-phosphate (shown in ...
(6S)-6-Fluoroshikimic acid is an antibacterial agent acting on the aromatic biosynthetic pathway. [1] It may be used against Plasmodium falciparum , the causative agent of malaria. [ 2 ] The molecule is targeting the enzymes of the shikimate pathway .
[23] [24] The aromatic amino acid phenylalanine, synthesized in the shikimic acid pathway, is the common precursor of phenol containing amino acids and phenolic compounds. In plants, the phenolic units are esterified or methylated and are submitted to conjugation , which means that the natural phenols are mostly found in the glycoside form ...
The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. [1] Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid , which is the central intermediate in ...
Polyphenols incorporate smaller parts and building blocks from simpler natural phenols, which originate from the phenylpropanoid pathway for the phenolic acids or the shikimic acid pathway for gallotannins and analogs. Flavonoids and caffeic acid derivatives are biosynthesized from phenylalanine and malonyl-CoA.
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.
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 ...