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Thursday, November 19, 2020 | History

1 edition of Synthetic transformations on shikimic acid found in the catalog.

Synthetic transformations on shikimic acid

Edward D. White

Synthetic transformations on shikimic acid

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  • 31 Currently reading

Published .
Written in English

    Subjects:
  • Physics

  • About the Edition

    Four strategies which involve synthetic elaboration of the shikimate nucleus are discussed. Methyl shikimate was differentially protected as the 3,4-0-cyclopentylidene ketal and as the 5-0-tert-butyldiphenylsilyl ether. The methyl ester was then reduced with diisobutylaluminum hydride and the resulting allylic alcohol was oxidized to aldehyde with pyridinium chlorochromate. The cyclopentylidene protecting group was removed to liberate the 3- and 4- hydroxyl groups which were acylated with maleic anhydride and succinic anhydride. The acylated aldehydes, as well as aldehyde were converted to their respective dimethlhydrazones.

    Edition Notes

    StatementEdward D. White III
    The Physical Object
    Pagination91 leaves.
    Number of Pages91
    ID Numbers
    Open LibraryOL25504538M

    A different type of advancement in this area can be illustrated in the commercial synthesis of oseltamivir (Tamiflu), a synthetic antiviral compound prescribed for avian flu that is made from shikimic acid. .


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Synthetic transformations on shikimic acid by Edward D. White Download PDF EPUB FB2

SYNTHETIC TRANSFORMATIONS ON (-)- SHIKIMIC ACID I. INTRODUCTION (-) -Shikimic acid (1) is a natural product of broad biological significance. It is known to occur in virtually all types of organisms and at all levels of the plant and animal kingdoms.

Specifically, (-)-shikimic acid. An illustration of an open book. Books. An illustration of two cells of a film strip. Video. An illustration of an audio speaker.

Audio. An illustration of a " floppy Synthetic transformations on shikimic acid book. Software. An illustration of two photographs. Synthetic transformations on shikimic acid. Synthetic transformations of shikimic acid Public Deposited.

Four strategies which involve synthetic elaboration of the shikimate nucleus are discussed. Methyl shikimate was differentially Author: Edward D. White. Title: Synthetic Transformations on Shikimic Acid.

By Sntmetic Tm, Shikiric Rcidcu, I Ehhhhhhhhhhhhls, Microcop Reouto Ts C, Luff L, Ln Edward, D. White Iii and Dr. -james D. White. Abstract. Four strategies which involve synthetic. Discusses both primary and secondary metabolites in relation to how they are influenced by shikimic acid.

Includes such topics as synthetic organic chemistry, enzymology of the common pathways in. About this book Focusing on biosynthesis, this book provides readers with approaches and methodologies for modern organic synthesis. By discussing major biosynthetic pathways and their chemical reactions, transformations, and natural products applications; it links biosynthetic mechanisms and more efficient total synthesis.

An epoxide derived from (−)-shikimic acid was attached to a solid support and used to synthesize over diverse small molecules. Key transformations include a Lewis acid-catalyzed. Shikimic acid is a phenolic acid which is known to possess several activities and it takes attention as a leading compound to some synthetic medicinal substances as well.

In this study, high performance liquid chromatographic analyses were carried out in order to determine shikimic acid. 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. Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic is an important biochemical metabolite in plants and microorganisms.

In-text: (CAINELLI and MANESCALCHI, ) Your Bibliography: CAINELLI, G. and MANESCALCHI, F., The Use of Anion-Exchange Resins in the Synthesis of Esters from.

Use shikimic acid as an anti-fungal treatment Shikimic acid has anti-fungal properties which make it an ideal anti-fungal treatment. According to a study that was published on the Korean Journal of Medical Mycology, the mechanism behind this activity is the ability of shikimic acid.

(6S)Fluoroshikimic acid 2 and (6R)hydroxyshikimic acid 3 have been synthesized via an OsO 4-catalysed dihydroxylation of diene 7, which was derived from (-)-shikimic acid 1. View Show abstract. e Shikimates Shikimic acid and quinic acid are useful synthons for the preparation of drugs (Chapter 15).

Both are plant products: shikimic acid from Illicium spp. and quinic acid from Cinchona spp. Yields are quite low, however.

Moreover, quinic acid. tivity to the individual amino acid (Herrmann, ). The number of isoenzymes and their sensitivities to the three aro- matic amino acids vary from microbe to microbe and have been used to define taxa.

routes from shikimic acid or quinic acid the supply problem first non‐shikimic or quinic acid synthetic routes synthesis of oseltamivir from cyclohexadiene derivatives building the. Figure 2 Effect of reaction time on transformation of quinic acid to shikimic acid by whole cells of B.

megaterium. 0 20 40 60 80 20 25 30 37 45 Bioconversion (%) Temperature (C) Figure 3 Effect of temperature on transformation of quinic acid to shikimic acid. Department of Chemistry, Aalto University, School of Chemical Technology, Espoo, Finland.

Search for more papers by this author. Synthetic Organic Chemistry and the Shikimate Pathway: Inhibitors and Intermediates Indoleacetic Acid, Its Synthesis and Regulation: A Basis for Tumorigenicity in Plant Disease Hydroxybenzoic Acids and the Enigma of Gallic Acid.

THE role of shikimic acid and related compounds in the biosynthesis of the aromatic ring by mutants of E. coli has recently been the subject of extensive study by Davis and his associates1.

Their. Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid. About this book Introduction The topic of the symposium, "The Shikimic Acid Pathway - Recent Advances", was especially appropriate for this, the Silver Anniversary of the Society because of the.

The impact of increased availability of phosphoenolpyruvate during shikimic acid biosynthesis has been examined in Escherichia coliK‐12 constructs carrying plasmid‐localized aroF FBR and tktAinserts encoding, respectively, feedback‐insensitive 3‐deoxy‐ d ‐arabino‐heptulosonic acid.

Shikimic acid (SA) produced from the seeds of Chinese star anise (Illicium verum) is a key intermediate for the synthesis of neuraminidase inhibitors such as oseltamivir (Tamiflu®), an anti. Shikimic acid (14) is a very attractive chiral building block for the synthesis of natural compounds.

However, due to the high cost (1 mol costs 13 Euro!, Aldrich ) and low availability, the synthetic utilization of shikimic acid is much more restricted in comparison with the less expensive quinic acid. Synthesis of shikimic acid 3-phosphate (S3P) The shikimate kinase enzyme (SK; EC ) catalyzes the phosphorylation of the shikimic acid, the fifth chemical reaction of the shikimate pathway, and the products are shikimic acid.

Due to its limited supply, searches for alternative synthetic routes preferably not requiring shikimic acid Oseltamivir total synthesis - Wikipedia The synthesis of tamiflu requires shikimic acid.

This acid is. While routes to (−)epi-shikimic acid 3 have been reported, 10 our goal was to devise a divergent synthetic strategy that could access any desired envisioned using a ring.

Abstract: Shikimic acid is a very important precursor for industrial synthesis of oseltamivir (Tamiflu ®) which is used for the antiviral this study, callus culture of Ginkgo biloba for shikimic acid. shikimic acid, a major biosynthetic precursor of aromatic a-amino acids, is sketched.

Because cisdihydroxylations can be performed with high diastereoselectiv- As will be shown throughout this book, the outcome of organic reactions is highly and more selective synthetic transformations. Shikimic acid is an intermediate in the common pathway of aromatic amino acid biosynthesis (Figure ), which begins with the condensation of phosphoenolpyruvic acid with d-erythrose 4-phosphate catalyzed by 3-deoxy-d- arabino -heptulosonic acid 7-phosphate (DAHP, Figure ) synthase.

COVID Resources. Reliable information about the coronavirus (COVID) is available from the World Health Organization (current situation, international travel).Numerous and frequently-updated. in the shikimic acid pathway were chosen for this study: benzoic acid, p-coumaric acid, vanillic acid, syringic acid, quinic acid, shikimic acid, orcinol monohydrate, and phenyl pyruvic acid (Figure 1).

We used zebra fish as our animal mod-el to verify the whitening capability of synthetic compounds in the shikimic acid. We obtained high yield transformations of the quinic acid skeleton, with formation of aromatic protocatechuic acid derivatives, during the course of our research work to develop antiviral drugs active against influenza viruses.

Compound 3, obtained from quinic acid 1, as described in Scheme A, was a key intermediate in our synthetic. Narendra Ambhaikar Shikimic acid 1/12/ CO2H HO OH OH (-)-shikimic acid-Shikimic acid is a hydroaromatic intermediate in the common pathway of aromatic amino acid biosynthesis.-First.

Background. Shikimic acid (3,4,5-trihydroxycyclohexenecarboxylic acid, SA), is a key chiral starting material for the synthesis of the antiviral neuraminidase inhibitor GS [1,2].It is a key. Focusing on biosynthesis, this book provides readers with approaches and methodologies for modern organic synthesis.

By discussing major biosynthetic pathways and their chemical reactions, transformations. tobacco plants (Ding et al., ). Shikimic acid is also a substrate for the hydroxycinnamoyl-CoA shikimic acid/ quinic acid hydroxycinnamoyltransferase (HCT) enzyme, which contributes significantly to lignification of plant leaves (Hoffmann et al., ).

These findings suggest that Shikimic acid. • Describes four major biosynthetic pathways (acetate, mevalonate, shikimic acid, and mixed pathways and alkaloids) and their related mechanisms • Covers reactions, tactics, and strategies for chemical transformations, linking biosynthetic processes and total synthesis • Includes strategies for optimal synthetic.

(-)-Shikimic acid for synthesis Synonym: (-)-Shikimic acid, (3R,4S,5R)-3,4,5-Trihydroxycyclohexenecarboxylic acid CAS Number Empirical Formula (Hill Notation) C 7 H 10 O 5.

ANAGNOSTOPOULOS C, CRAWFORD IP. Transformation studies on the linkage of markers in the tryptophan pathway in Bacillus subtilis. Proc Natl Acad Sci U S A. Mar 15; – [PMC free article] [] [Google Scholar]ARCAMONE F, CHAIN EB, FERRETTI A, PENNELLA P. Formation of 2,3-dihydroxybenzoic acid in fermentation liquors during the submerged culture production of lysergic acid .After transformation into carboxylic a During the synthetic study of 62 First total synthesis of (−)-pericosine A from (−)-shikimic acid: Structure Revision and determination of the .As a result, the cost of raw shikimic acid can vary by up to per cent, depending on whether a flu outbreak is imminent.

Since then, scientists have been focusing on alternative sources of.