3-Dehydroshikimic acid is a chemical compound related to shikimic acid. 3-DHS is available in large quantity through engineering of the shikimic acid pathway.[1]
^Banwell, M. G.; Edwards, A. J.; Essers, M.; Jolliffe, K. A. (2003). "Conversion of (−)-3-Dehydroshikimic Acid into Derivatives of the (+)-Enantiomer". The Journal of Organic Chemistry. 68 (17): 6839–6841. doi:10.1021/jo034689c. PMID 12919063.
^Dewick, P. M.; Haslam, E. (1969). "Phenol biosynthesis in higher plants. Gallic acid". The Biochemical Journal. 113 (3): 537–542. doi:10.1042/bj1130537. PMC1184696. PMID 5807212.
^Muir, R. M.; Ibáñez, A. M.; Uratsu, S. L.; Ingham, E. S.; Leslie, C. A.; McGranahan, G. H.; Batra, N.; Goyal, S.; Joseph, J.; Jemmis, E. D.; Dandekar, A. M. (2011). "Mechanism of gallic acid biosynthesis in bacteria (Escherichia coli) and walnut (Juglans regia)". Plant Molecular Biology. 75 (6): 555–565. doi:10.1007/s11103-011-9739-3. PMC3057006. PMID 21279669.
September 01, 2023
dehydroshikimic, acid, chemical, compound, related, shikimic, acid, available, large, quantity, through, engineering, shikimic, acid, pathway, namespreferred, iupac, name, dihydroxy, oxocyclohex, carboxylic, acidother, names, dehydroshikimate3, dhsidentifiersc. 3 Dehydroshikimic acid is a chemical compound related to shikimic acid 3 DHS is available in large quantity through engineering of the shikimic acid pathway 1 3 Dehydroshikimic acid NamesPreferred IUPAC name 4S 5R 4 5 Dihydroxy 3 oxocyclohex 1 ene 1 carboxylic acidOther names 3 Dehydroshikimate3 DHS 3 DHSIdentifiersCAS Number 2922 42 1 Y3D model JSmol Interactive imageChEBI CHEBI 30918 YChemSpider 388830ECHA InfoCard 100 162 474PubChem CID 439774InChI InChI 1S C7H8O5 c8 4 1 3 7 11 12 2 5 9 6 4 10 h1 5 6 9 10H 2H2 H 11 12 t5 6 m1 s1Key SLWWJZMPHJJOPH PHDIDXHHSA NInChI 1 C7H8O5 c8 4 1 3 7 11 12 2 5 9 6 4 10 h1 5 6 9 10H 2H2 H 11 12 t5 6 m1 s1Key SLWWJZMPHJJOPH PHDIDXHHBWSMILES C1 C H C H C O C C1C O O O OPropertiesChemical formula C 7H 8O 5Molar mass 172 136 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesMetabolism EditBiosynthesis The enzyme 3 dehydroquinate dehydratase uses 3 dehydroquinate to produce 3 dehydroshikimate and H2O 3 Dehydroshikimate is then reduced to shikimic acid by the enzyme shikimate dehydrogenase which uses nicotinamide adenine dinucleotide phosphate NADPH as a cofactor nbsp Biosynthesis of shikimic acid from 3 dehydroquinateGallic acid is also formed from 3 dehydroshikimate by the action of the enzyme shikimate dehydrogenase to produce 3 5 didehydroshikimate This latter compound spontaneously rearranges to gallic acid 2 3 4 References Edit Banwell M G Edwards A J Essers M Jolliffe K A 2003 Conversion of 3 Dehydroshikimic Acid into Derivatives of the Enantiomer The Journal of Organic Chemistry 68 17 6839 6841 doi 10 1021 jo034689c PMID 12919063 Gallic acid pathway on metacyc org Dewick P M Haslam E 1969 Phenol biosynthesis in higher plants Gallic acid The Biochemical Journal 113 3 537 542 doi 10 1042 bj1130537 PMC 1184696 PMID 5807212 Muir R M Ibanez A M Uratsu S L Ingham E S Leslie C A McGranahan G H Batra N Goyal S Joseph J Jemmis E D Dandekar A M 2011 Mechanism of gallic acid biosynthesis in bacteria Escherichia coli and walnut Juglans regia Plant Molecular Biology 75 6 555 565 doi 10 1007 s11103 011 9739 3 PMC 3057006 PMID 21279669 Retrieved from https en wikipedia org w index php title 3 Dehydroshikimic acid amp oldid 1170996132, wikipedia, wiki, book, books, library,