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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
The systematic name of this enzyme class is 3-dehydroquinate hydro-lyase (3-dehydroshikimate-forming). This enzyme is one of the few examples of convergent evolution. The two separate versions of this enzyme have different amino acid sequences. [2] 3-Dehydroquinate dehydratase is also commonly referred to as Dehydroquinate dehydratase and DHQD ...
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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(2) shikimate + NAD(P) + 3-dehydroshikimate + NAD(P)H + H + This is the second shikimate dehydrogenase enzyme found in Escherichia coli and differs from EC 1.1.1.25 , shikimate dehydrogenase, in that it can use both quinate and shikimate as substrate, and either NAD + or NADP + as acceptor.
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.
Like [1.1.1]propellane, 1,3-dehydroadamantane can be polymerized by breaking the axial bond and joining the resulting radicals into a linear chain: Scheme 2: Polymerization of 1,3-dehydroadamantane. In this scheme, 1,3-dehydroadamantane is reacted with acrylonitrile in a radical polymerization initiated with lithium metal in tetrahydrofuran.