138-59-0Relevant articles and documents
Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid
Jiang, Shende,McCullough, Kevin J.,Mekki, Boualem,Singh, Gurdial,Wightman, Richard H.
, p. 1805 - 1814 (1997)
Diastereoselective reaction of 2,3-O-isopropylidene-D-ribose with allylmagnesium chloride gave a 5 : 1 mixture of triols 4 and 5, which were then converted to nitrones 8 and 9. Intramolecular nitrone cycloaddition gave the isoxazolidines 10 and 11, which on acetylation gave the corresponding acetates 12 and 13 which were separated by repeated crystallisation. The major adduct 12 was converted to (-)-5-epi-shikimic acid 2. Reaction of the ribonolactone derivative 20 with allylmagnesium chloride gave the hemiacetal 21. Reduction of compound 21 with DIBAL afforded exclusively the diol 22, which was desilylated to give the triol 5. Similar chemistry to that employed for the synthesis of (-)-5-epi-shikimic acid 2 with the diol 5 resulted in the synthesis of (-)-shikimic acid 1.
Chemical and toxicological studies on bracken fern, Pteridium aquilinum var. latiusculum. VI. Isolation of 5-O-caffeoylshikimic acid as an antithiamine factor
Fukuoka
, p. 3219 - 3224 (1982)
5-O-Caffeoylshikimic acid (dactylifric acid) was isolated from bracken fern as a major constituent of its acutely toxic fraction, which causes depression of leucocytes and thrombocytes in calves. 5-O-Caffeoylshikimic acid exhibited an antithiamine effect in vitro, but had no hematuric effect in guinea pigs.
Hydroaromatic equilibration during biosynthesis of shikimic acid
Knop,Draths,Chandran,Barker,Von Daeniken,Weber,Frost
, p. 10173 - 10182 (2001)
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.
Synthesis of aminoshikimic acid
Guo, Jiantao,Frost
, p. 1585 - 1588 (2004)
5-Amino-5-deoxyshikimic acid (aminoshikimic acid) was synthesized from glucose using recombinant Amycolatopsis mediterranei and also synthesized by a tandem, two-microbe route employing Bacillus pumilus and recombinant Escherichia coli.
An enantioconvergent route to (-)-shikimic acid via a palladium-mediated elimination reaction
Yoshida, Naoyuki,Ogasawara, Kunio
, p. 1461 - 1463 (2000)
(Matrix presented) (-)-Shikimic acid, the key intermediate in the shikimate pathway in plants and microorganisms, has been synthesized in an enantioconvergent manner from both enantiomeric starting materials by employing a palladium-mediated elimination reaction as the key step.
Enantiospecific synthesis of (-)-5-epi-shikimic acid and a new route to (-)-shikimic acid
Jiang, Shende,Mekki, Boualem,Singh, Gurdial,Wightman, Richard H.
, p. 5505 - 5508 (1994)
(-)-Shikimic acid (1) and (-)-5-epi-shikimic acid (2) have each been prepared enantiospecifically and with high diastereoselectivity from D-ribose.
New phenolic compounds from Meehania urticifolia
Murata, Toshihiro,Miyase, Toshio,Yoshizaki, Fumihiko
, p. 385 - 390 (2011)
A new phenylethanoid glycoside, rashomoside A (1), a new phenolic glucoside, rashomoside B (2), and a new shikimic acid derivative (3) were isolated from Meehania urticifolia together with 12 known flavones (4-15), three known phenylethanoid glycosides (16-18), and 13 other compounds (19-31). The structure of each of these compounds was elucidated based on the results of spectroscopic analysis.
Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules
He, Yun-Gang,Huang, Yong-Kang,Xu, Zhang-Li,Xie, Wen-Jing,Luo, Yong-Qiang,Li, Feng-Lei,Zhu, Xing-Liang,Shi, Xiao-Xin
, p. 4318 - 4332 (2021/07/21)
Novel stereodivergent total syntheses of all the seven stereoisomers of (?)-shikimic acid [(?)-SA 1] have been systematically performed. (+)-ent-SA ent-1 was synthesized from (?)-SA 1 via 9 steps in 31 % overall yield; (?)-3-epi-SA 2 was synthesized from (?)-SA 1 via 5 steps in 66 % overall yield; (+)-3-epi-ent-SA ent-2 was synthesized from (?)-SA 1 via 7 steps in 43 % overall yield; (?)-4-epi-SA 3 was synthesized from (?)-SA 1 via 11 steps in 32 % overall yield; (+)-4-epi-ent-SA ent-3 was synthesized from (?)-SA 1 via 7 steps in 42 % overall yield; (?)-5-epi-SA 4 was synthesized from (?)-SA 1 via 6 steps in 56 % overall yield; and (+)-5-epi-ent-SA ent-4 was synthesized from (?)-SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (?)-SA 1 were further studied by two dimensional (2D) 1H NMR technique.
A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol
Ananthan, Bakthavachalam,Chang, Wan-Chun,Lin, Jhe-Sain,Li, Pin-Hui,Yan, Tu-Hsin
, p. 2898 - 2905 (2014/05/06)
Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.
Medicinal flowers. XXX. Eight new glycosides, everlastosides F - M, from the flowers of Helichrysum arenarium
Morikawa, Toshio,Wang, Li-Bo,Ninomiya, Kiyofumi,Nakamura, Seikou,Matsuda, Hisashi,Muraoka, Osamu,Wu, Li-Jun,Yoshikawa, Masayuki
experimental part, p. 853 - 859 (2010/03/26)
Eight new glycosides, everlastosides F (1), G (2), H (3), I (4), J (5), K (6), L (7), and M (8), were isolated from the methanolic extract of the flowers of Helichrysum arenarium. Their structures were elucidated on the basis of chemical and physicochemic
