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Biosynthesis: The enzyme 3-dehydroquinate dehydratase uses 3-dehydroquinate to produce 3-dehydroshikimate and H 2 O. 3-Dehydroshikimate is then reduced to shikimic acid by the enzyme shikimate dehydrogenase, which uses nicotinamide adenine dinucleotide phosphate (NADPH) as a cofactor. Biosynthesis of shikimic acid from 3-dehydroquinate
3-dehydroshikimate dehydratase (EC 4.2.1.118) is an enzyme with systematic name 3-dehydroshikimate hydro-lyase. [ 1 ] [ 2 ] This enzyme catalyses the following chemical reaction 3-dehydro-shikimate ⇌ {\displaystyle \rightleftharpoons } 3,4-dihydroxybenzoate + H 2 O
In enzymology, a shikimate dehydrogenase (EC 1.1.1.25) is an enzyme that catalyzes the chemical reaction shikimate + NADP + ⇌ {\displaystyle \rightleftharpoons } 3-dehydroshikimate + NADPH + H + Thus, the two substrates of this enzyme are shikimate and NADP + , whereas its 3 products are 3-dehydroshikimate , NADPH , and H + .
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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 the figure below). [1] [2] Shikimate 3-phosphate is then coupled with phosphoenol pyruvate to give 5-enolpyruvylshikimate-3-phosphate via the enzyme 5-enolpyruvylshikimate-3-phosphate ...
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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.