Abstract. The shikimic acid pathway is responsible for the biosynthesis of many aromatic compounds by a broad range of organisms, including. IT has been assumed generally, without adequate supporting evidence, that tryptophan and other indole compounds are generated via the shikimic acid. The shikimate pathway (shikimic acid pathway) is a seven step metabolic route used by bacteria, archaea, fungi, algae, some protozoan, and plants for the biosynthesis of folates and aromatic amino acids (phenylalanine, tyrosine, and tryptophan).
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Shikimic acid - Wikipedia
XLS 38K Additional file 10 Genetic architecture of the shikimic acid pathway across a range of taxonomically different prokaryote genomes shows that the genes encoding the pathway are not clustered.
Abstract Background A central tenet in biochemistry for over 50 years has held that microorganisms, plants and, more recently, certain apicomplexan parasites synthesize essential aromatic compounds via elaboration of a complete shikimic acid pathway, shikimic acid pathway metazoans lacking this pathway require a dietary source of these compounds.
The large number of sequenced bacterial and archaean genomes now available for comparative genomic analyses allows the fundamentals of this contention to be tested in prokaryotes. Using Hidden Markov Model profiles HMM profiles to identify all known enzymes of the pathway, we report the presence of genes encoding shikimate pathway enzymes in shikimic acid pathway hypothetical proteomes constructed from the genomes of sequenced prokaryotes.
Results Amongst free-living prokaryotes shikimic acid pathway Bacteria possess, as expected, genes encoding a complete shikimic acid pathway, whereas of the culturable Archaea, only one was found to have a shikimic acid pathway complement of recognisable enzymes in its predicted proteome.
It may be that in the Archaea, the primary amino-acid sequences of enzymes of the pathway are highly divergent and so are not detected by HMM profiles.
Alternatively, structurally unrelated non-orthologous proteins might be performing the same biochemical functions as those encoding recognized genes of the shikimate pathway.
Shikimate pathway - Wikipedia
Many of these microbes show some degree of genome reduction, suggesting that these host-associated bacteria might sequester essential aromatic compounds from a parasitised shikimic acid pathway, as a 'shared metabolic adaptation' in mutualistic symbiosis, or obtain them from other consorts having the complete biosynthetic pathway.
The phenylpropanoids are then used to produce the flavonoidscoumarinstannins and lignin.
The first enzyme involved is phenylalanine ammonia-lyase PAL that converts L- phenylalanine to trans- cinnamic acid and ammonia. Gallic acid biosynthesis Gallic acid shikimic acid pathway formed from 3-dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3,5-didehydroshikimate.
This latter compound shikimic acid pathway rearranges to shikimic acid pathway acid. Uses[ edit ] In the pharmaceutical industry, shikimic acid from the Chinese star anise Illicium verum is used as a base material for production of oseltamivir Tamiflu.
Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and in general found in very low concentrations.
The low isolation yield of shikimic acid from the Chinese star anise is blamed for the shortage of oseltamivir. Shikimic acid can also be extracted from the seeds of the sweetgum Liquidambar styraciflua fruit,  which is abundant in North America, in yields of around 1.
Biosynthetic pathways in E. However, the availability of a cheap chiral building block can overcome these additional costs e.
Aminoshikimic acid is also an alternative to shikimic acid as a starting material for the synthesis of oseltamivir.