Stereospecific Synthesis of Optically Pure Quinic Acid and Shikimic Acid from <scp>D</scp>‐Arabinose

Bestmann, Hans Jürgen; Heid, H.

doi:10.1002/anie.197103362

Cited by 21 publications

(7 citation statements)

References 15 publications

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“…Our approach to [7-l4C]shikimic acid (Scheme II) elaborated a reported sequence (Grewe and Vangermain, 1965) with modifications because of the unexpected presence of nitrile 15 from which [7-14C]-4-ep/-shikimic acid ( 16) could be obtained.2 The advantage of this approach is that by utilizing quinic acid (10) as a starting material the stereochemistry of the future trihydroxycyclohexene system is predetermined assuming no racemization during the sequence. The latter assumption has been verified in that shikimic acid with total retention of optical activity has been obtained from the overall process (Bestmann and Heid, 1971).…”

Section: Resultsmentioning

confidence: 83%

Biosynthesis of bacterial menaquinones. Dissymmetry in the naphthalenic intermediate

Baldwin¹,

Snyder²,

Rapoport³

1974

Biochemistry

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Section: Resultsmentioning

confidence: 83%

Biosynthesis of bacterial menaquinones. Dissymmetry in the naphthalenic intermediate

Baldwin¹,

Snyder²,

Rapoport³

1974

Biochemistry

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“…Sugars have been reported as suitable naturally occurring starting materials for the synthesis of enantiopure shikimic acid. Heid et al 139 took advantage of the stereochemistry of D-arabinose and were the first to report stereospecific synthesis of (−)-shikimic acid from the sugar platform (Scheme 37). Later, Kitagawa et al 140 demonstrated the synthesis of the key intermediate 14 from Dmannose (Scheme 38).…”

Section: Chemical Reviewsmentioning

confidence: 99%

Production and Synthetic Modifications of Shikimic Acid

2018

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Shikimic acid is a natural product of industrial importance utilized as a precursor of the antiviral Tamiflu. It is nowadays produced in multihundred ton amounts from the extraction of star anise (Illicium verum) or by fermentation processes. Apart from the production of Tamiflu, shikimic acid has gathered particular notoriety as its useful carbon backbone and inherent chirality provide extensive use as a versatile chiral precursor in organic synthesis. This review provides an overview of the main synthetic and microbial methods for production of shikimic acid and highlights selected methods for isolation from available plant sources. Furthermore, we have attempted to demonstrate the synthetic utility of shikimic acid by covering the most important synthetic modifications and related applications, namely, synthesis of Tamiflu and derivatives, synthetic manipulations of the main functional groups, and its use as biorenewable material and in total synthesis. Given its rich chemistry and availability, shikimic acid is undoubtedly a promising platform molecule for further exploration. Therefore, in the end, we outline some challenges and promising future directions.

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“…4,13,52 Although several routes have been described for chemical synthesis, production of SA acid by these methods is too expensive and/or generates waste containing environmental pollutants; therefore, these are not commercially viable. 4,10,[53][54][55][56][57][58][59] Because plants synthesize aromatic amino acids and most polycyclic compounds by their SA pathway, the yield of SA from this source can vary; the factors that influence the yield include the time of harvest, handling, storage, plant tissue, and other factors that regulate plant metabolism resulting in the accumulation of SA in tissues where metabolic processes have slowed or stopped, such as seeds and fruits. 60,61 Plants of the Illicium spp.…”

Section: Sa Production Extraction From Plant Sourcesmentioning

confidence: 99%

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

Quiroz¹,

Carmona²,

Bolívar³

et al. 2014

RRMC

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Aromatic metabolism comprises the shikimic acid (SA) and the aminoshikimic acid (ASA) pathways. The SA pathway is the common route for the biosynthesis of aromatic amino acids and other metabolites in bacteria, higher plants, fungi, and Apicomplexa parasites, but this pathway is absent in mammals. A variant of the SA pathway known as the ASA pathway branches off from the normal pathway in some bacteria, and its final product, 3-amino-5-hydroxybenzoic acid, is the precursor for many aminoglycoside antibiotics such as kanamycin, neomycin, butirosin, and spectinomycin. The SA pathway includes the key intermediate SA, which is the precursor for the chemical synthesis of the drug oseltamivir phosphate, known commercially as Tamiflu ® , an efficient inhibitor of the neuraminidase enzyme of the seasonal influenza viruses types A and B, avian influenza virus H5N1, and human influenza virus H1N1. Meanwhile, the intermediate of the ASA pathway, ASA, is an attractive candidate for use as the core scaffold for the synthesis of combinatorial libraries and is a potential alternative to SA as a precursor for oseltamivir phosphate synthesis. In this review, we discuss the relevance of the key intermediates SA and ASA as scaffold molecules for the synthesis of diverse chemicals. We highlight the current and potential pharmaceutical applications of these molecules and discuss the main strategies for the production of these aromatic compounds from natural sources and the application of metabolic engineering strategies in diverse bacterial strains for production through biotechnological processes.

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Stereospecific Synthesis of Optically Pure Quinic Acid and Shikimic Acid from D‐Arabinose

Cited by 21 publications

References 15 publications

Biosynthesis of bacterial menaquinones. Dissymmetry in the naphthalenic intermediate

Biosynthesis of bacterial menaquinones. Dissymmetry in the naphthalenic intermediate

Production and Synthetic Modifications of Shikimic Acid

Current perspectives on applications of shikimic and aminoshikimic acids in pharmaceutical chemistry

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