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Query: CAS:77-95-2 ((-)-quinic acid)
 128 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

The expense and limited availability of shikimic acid isolated from plants has impeded utilization of this hydroaromatic as a synthetic starting material. Although recombinant Escherichia coli catalysts have been constructed that synthesize shikimic acid from glucose, the yield, titer, and purity of shikimic acid are reduced by the sizable concentrations of quinic acid and 3-dehydroshikimic acid that are formed as byproducts. The 28.0 g/L of shikimic acid synthesized in 14% yield by E. coli SP1.1/pKD12.138 in 48 h as a 1.6:1.0:0.65 (mol/mol/mol) shikimate/quinate/dehydroshikimate mixture is typical of synthesized product mixtures. Quinic acid formation results from the reduction of 3-dehydroquinic acid catalyzed by aroE-encoded shikimate dehydrogenase. Is quinic acid derived from reduction of 3-dehydroquinic acid prior to synthesis of shikimic acid? Alternatively, does quinic acid result from a microbe-catalyzed equilibration involving transport of initially synthesized shikimic acid back into the cytoplasm and operation of the common pathway of aromatic amino acid biosynthesis in the reverse of its normal biosynthetic direction? E. coli SP1.1/pSC5.214A, a construct incapable of de novo synthesis of shikimic acid, catalyzed the conversion of shikimic acid added to its culture medium into a 1.1:1.0:0.70 molar ratio of shikimate/quinate/dehydroshikimate within 36 h. Further mechanistic insights were afforded by elaborating the relationship between transport of shikimic acid and formation of quinic acid. These experiments indicate that formation of quinic acid during biosynthesis of shikimic acid results from a microbe-catalyzed equilibration of initially synthesized shikimic acid. By apparently repressing shikimate transport, the aforementioned E. coli SP1.1/pKD12.138 synthesized 52 g/L of shikimic acid in 18% yield from glucose as a 14:1.0:3.0 shikimate/quinate/dehydroshikimate mixture.
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PMID:Hydroaromatic equilibration during biosynthesis of shikimic acid. 1160 66

3-Dehydroquinate production from quinate by oxidative fermentation with Gluconobacter strains of acetic acid bacteria was analyzed for the first time. In the bacterial membrane, quinate dehydrogenase, a typical quinoprotein containing pyrroloquinoline quinone (PQQ) as the coenzyme, functions as the primary enzyme in quinate oxidation. Quinate was oxidized to 3-dehydroquinate with the final yield of almost 100% in earlier growth phase. Resting cells, dried cells, and immobilized cells or an immobilized membrane fraction of Gluconobacter strains were found to be useful biocatalysts for quinate oxidation. 3-Dehydroquinate was further converted to 3-dehydroshikimate with a reasonable yield by growing cells and also immobilized cells. Strong enzyme activities of 3-dehydroquinate dehydratase and NADP-dependent shikimate dehydrogenase were detected in the soluble fraction of the same organism and partially fractionated from each other. Since the shikimate pathway is remote from glucose in the metabolic pathway, the entrance into the shikimate pathway from quinate to 3-dehydroquinate looks advantageous to produce metabolic intermediates in the shikimate pathway.
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PMID:3-dehydroquinate production by oxidative fermentation and further conversion of 3-dehydroquinate to the intermediates in the shikimate pathway. 1458 99

Kiwifruit are novel in that they contain high levels of quinic acid (1-2% w/w), which contributes to the flavour, sugar/acid balance and health-giving properties of the fruit. In a study of quinic acid storage and metabolism in three kiwifruit species (Actinidia chinensis Planch. var. chinensis, Actinidia deliciosa (A. Chev.) C.F. Liang et A.R. Ferguson var. deliciosa and Actinidia arguta (Sieb. et Zucc.) Planch. ex Miq. var. arguta) quinic acid accumulation occurred principally in the early stages (<60 days after anthesis; (DAA)) of fruit development. The present study established that there are separate quinate dehydrogenase (QDH) and shikimate dehydrogenase (SDH) activities in kiwifruit, probably representing different proteins. Quinate dehydrogenase activity was at a maximum around the time of greatest quinic acid accumulation and declined markedly in late fruit development, and was also higher in the species that accumulated the largest amounts of quinic acid (A. chinensis and A. deliciosa). In contrast, SDH activity was highest in the early stages of fruit development and only declined to 30-50% at later stages of fruit development in all three species. Dehydroquinate synthase gene expression levels measured by quantitative real-time PCR showed a high level in the early season, which was sustained through the mid-season. The quantitative real-time PCR results for a kiwifruit EST that had homology to chloroplastic isoforms of SDH showed an induction in the middle to late season; therefore, the high level of SDH activity in the early season (<30 DAA) may have resulted from the expression of a cytosolic isoform of the enzyme. The results are also consistent with the relative levels of the bifunctional dehydroquinate dehydratase/SDH enzyme and QDH enzyme controlling the accumulation and utilisation of quinic acid in kiwifruit.
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PMID:Changes in quinic acid metabolism during fruit development in three kiwifruit species. 3268 60