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Shikimate

The initial step in the pathway is the condensation of erythrose-4-phosphale with phosphoenolpyruvate, yielding dehydroquinic acid, which by elimination of the elements of water affords dehydroshikimic acid reduction of the 3-keto group to hydroxyl gives shikimic acid. [Pg.357]

Diacetoxylation of various conjugated dienes including cyclic dienes has been extensively studied. 1,3-Cyclohexadiene was converted into a mixture of isomeric l,4-diacetoxy-2-cyclohexenes of unknown stereochemistry[303]. The stereoselective Pd-catalyzed 1,4-diacetoxylation of dienes is carried out in AcOH in the presence of LiOAc and /or LiCI and beiizoquinone[304.305]. In the presence of acetate ion and in the absence of chloride ion, /rau.v-diacetox-ylation occurs, whereas addition of a catalytic amount of LiCl changes the stereochemistry to cis addition. The coordination of a chloride ion to Pd makes the cis migration of the acetate from Pd impossible. From 1,3-cyclohexadiene, trans- and ci j-l,4-diacetoxy-2-cyclohexenes (346 and 347) can be prepared stereoselectively. For the 6-substituted 1,3-cycloheptadiene 348, a high diaster-eoselectivity is observed. The stereoselective cij-diacetoxylation of 5-carbo-methoxy-1,3-cyclohexadiene (349) has been applied to the synthesis of dl-shikimic acid (350). [Pg.68]

Phenylalanine- and Tyrosine-Derived Alkaloids. Carbohydrate metaboHsm leads via a seven-carbon sugar, ie, a heptulose, derivative to shikimic acid [138-59-0] (57), C H qO, which leads in turn to prephenic acid [126-49-8] (58), (43). [Pg.539]

The mode of action is by inhibiting 5-enolpymvyl-shikimate-3-phosphate synthase. Roundup shuts down the production of the aromatic amino acids phenylalanine, tyrosine, and tryptophane (30). Whereas all these amino acids are essential to the survival of the plant, tryptophane is especially important because it is the progenitor for indole-3-acetic acid, or auxin, which plays an important role in growth and development, and controls cell extension and organogenesis. [Pg.421]

E. E. Conn, The Shikimic Acid Pathway, Plenum Press, New York, 1986. [Pg.58]

The ansa-chain of the ansamycins streptovaricins (4), rifamycins (263), geldanamycin (4), and herbimycin (32) has been shown to be polyketide in origin, being made up of propionate and acetate units with the 0-methyl groups coming from methionine. The remaining aromatic C N portion of the ansamacroHdes is derived from 3-amino-5-hydroxybenzoic acid (264—266) which is formed via shikimate precursors. Based on the precursors of the rifamycins and streptovaricins isolated from mutant bacteria strains, a detailed scheme for the biosynthesis of most of the ansamacroHdes has been proposed (95,263). [Pg.506]

Biosynthesis of Tea Flavonoids. The pathways for the de novo biosynthesis of flavonoids in both soft and woody plants (Pigs. 3 and 4) have been generally elucidated and reviewed in detail (32,51). The regulation and control of these pathways in tea and the nature of the enzymes involved in synthesis in tea have not been studied exhaustively. The key enzymes thought to be involved in the biosynthesis of tea flavonoids are 5-dehydroshikimate reductase (52), phenylalanine ammonia lyase (53), and those associated with the shikimate/arogenate pathway (52). At least 13 enzymes catalyze the formation of plant flavonoids (Table 4). [Pg.368]

Vitamins are classified by their solubiUty characteristics iato fat-soluble and water-soluble groups. The fat-soluble vitamins A, E, and K result from the isoprenoid biosynthetic pathway. Vitamin A is derived by enzymic cleavage of the symmetrical C q beta-carotene, also known as pro-vitamin A. Vitamins E and K result from condensations of phytyldiphosphate (C2q) with aromatic components derived from shikimic acid. Vitamin D results from photochemical ring opening of 7-dehydrocholesterol, itself derived from squalene (C q). [Pg.5]

Animals caimot synthesize the naphthoquinone ring of vitamin K, but necessary quantities are obtained by ingestion and from manufacture by intestinal flora. In plants and bacteria, the desired naphthoquinone ring is synthesized from 2-oxoglutaric acid (12) and shikimic acid (13) (71,72). Chorismic acid (14) reacts with a putative succinic semialdehyde TPP anion to form o-succinyl benzoic acid (73,74). In a second step, ortho-succmY benzoic acid is converted to the key intermediate, l,4-dihydroxy-2-naphthoic acid. Prenylation with phytyl pyrophosphate is followed by decarboxylation and methylation to complete the biosynthesis (75). [Pg.155]

The earliest references to cinnamic acid, cinnamaldehyde, and cinnamyl alcohol are associated with thek isolation and identification as odor-producing constituents in a variety of botanical extracts. It is now generally accepted that the aromatic amino acid L-phenylalanine [63-91-2] a primary end product of the Shikimic Acid Pathway, is the precursor for the biosynthesis of these phenylpropanoids in higher plants (1,2). [Pg.173]

P/Z equilibrium 233 enantioselectivity 216 endo 153 endo isomer 217 endo/exo ratio 303 endo/exo selectivity 217 mt-shikimic acid 30 ethyl vinyl ether 220 exo 153 exo-endo 303 exo-selective 13... [Pg.330]

The first known pseudo-hexose, pseudo-a-DL-toZopyranose (34) was prepared by reduction of the keto-acid monoacetate (30) 26, 27). This intermediate, which had been used by Daniels, Doshi, and Smissman (9, JO) for a synthesis of shikimic acid, is prepared from the Diels-Alder adduct (31) of 2-acetoxyfuran and maleic anhydride, by a remarkable series of transformations. [Pg.60]

Dehydroquinic acid and [l,6-14C]-D-shikimic acid methyl ester were not incorporated, indicating a very early branch from the shikimate pathway. The intermediacy of 4-amino-3,4-dideoxy-D-araf>ino-heptulosonic acid 7-phosphate (37) was proposed, consistent with later findings on the role of the variant aminoshikimate pathway [94]. [Pg.408]

Shi epoxidation 283 Shibasald 234, 236, 242 Shikimate pathway 407 [3,3]-sigmatropic rearrangement 51 silicon-lithium exchange 157 single-carbon homologation... [Pg.489]

The organism utilized is a mutant of E. coli blocked in the synthesis of aromatic amino acids before the shikimate step. Cells are first grown in the presence of adenosine, a technique that temporarily derepresses the system of en-... [Pg.275]

C3H9N3O2 64616-76-8) see Benserazide D-serine methyl ester hydrochloride (C4H,()C N03 5874-57-7) sec Cycloserine A -(DL-seryl)-2,3,4-trihydroxybenzaldehyde hydrazone (CJ0H13N3O5) see Benserazide (-)-shikimic acid... [Pg.2440]

Optically pure quinic and shikimic acids have been synthesized starting from o-arabinose. The key steps involved treatment of the bis-tosylate (162) with 3 mol of methylenetriphenylphosphorane to give the ylide (163) which with formaldehyde gave the olefin (164) in 82% yield overall. [Pg.178]

Quinones represent a very large and heterogeneous class of biomolecules. Three major biosynthetic pathways contribute to the formations of various quinones. The aromatic skeletons of quinones can be synthesized by the polyketide pathway and by the shikimate pathway. The isoprenoid pathways are involved in the biosynthesis of the prenyl chain and in the formation of some benzoquinones and naphthoquinones. ... [Pg.102]

The shikimate pathway is the major route in the biosynthesis of ubiquinone, menaquinone, phyloquinone, plastoquinone, and various colored naphthoquinones. The early steps of this process are common with the steps involved in the biosynthesis of phenols, flavonoids, and aromatic amino acids. Shikimic acid is formed in several steps from precursors of carbohydrate metabolism. The key intermediate in quinone biosynthesis via the shikimate pathway is the chorismate. In the case of ubiquinones, the chorismate is converted to para-hydoxybenzoate and then, depending on the organism, the process continues with prenylation, decarboxylation, three hydroxy-lations, and three methylation steps. - ... [Pg.102]


See other pages where Shikimate is mentioned: [Pg.21]    [Pg.97]    [Pg.327]    [Pg.357]    [Pg.357]    [Pg.897]    [Pg.883]    [Pg.252]    [Pg.253]    [Pg.45]    [Pg.351]    [Pg.363]    [Pg.30]    [Pg.30]    [Pg.407]    [Pg.408]    [Pg.291]    [Pg.1505]    [Pg.1506]    [Pg.1506]    [Pg.1506]    [Pg.2380]    [Pg.2382]    [Pg.2384]    [Pg.121]    [Pg.168]    [Pg.203]    [Pg.188]    [Pg.129]    [Pg.87]   
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5-enolpyruvyl shikimate 3-phosphate synthase EPSPS)

Acetate-shikimate biosynthesis

Acids shikimic acid

Aerobacter aerogenes shikimate pathway

Amino acid synthesis shikimate

Amino acids shikimic acid pathway

Anthranilic acid shikimate pathway

Antibiotics shikimic acid derive

Antibiotics shikimic acid derived

Arabidopsis shikimate pathway

Aroma compounds shikimates

Aromatic amino acids shikimate pathway

Biosynthesis of Shikimic Acid

Biosynthesis shikimate pathway

Biosynthetic pathways Shikimic acid

Coumarine shikimate-derived

Enolpyruvate shikimate-3-phosphate

Enolpyruvyl shikimate-3-phosphate

Enolpyruvyl shikimate-3-phosphate synthase

Ent-Shikimic acid

Erythrose 4-phosphate, shikimic acid pathway

Escherichia coli shikimate pathway

Expansion of the Shikimate Pathway in Terrestrial Plants

Genetic engineering shikimate pathway

Glyphosate shikimate accumulation

Glyphosate shikimic acid accumulation

Hydroxycinnamoyl-CoA shikimate

Hydroxycinnamoyl-CoA shikimate/quinate

Illicium religiosum [Shikimic acid

Methyl shikimate

Methyl shikimate synthesis

Methyl shikimate via cyclohexadienyl complexes

Mutants shikimic acid pathway

Naphthoquinones and Anthraquinones Derived from Shikimic Acid

Natural products originating from shikimic acid

Neurospora shikimate pathway

Of shikimic acid

Phenolic Compounds Derived from Shikimate

Phenolics shikimate pathway

Phenylpropanoids from shikimic acid pathway

Phenylpropanoids shikimate pathway

Phosphoenolpyruvate, shikimic acid pathway

Prephenate, intermediates shikimic acid pathway

Primary Metabolism of Shikimic Acid and Aromatic Amino Acids

Primary metabolism shikimic acid

Quinic and Shikimic Acids

Repression of the Shikimic Acid Pathway

Shikimate 3-phosphase Synthase (EPSPS)

Shikimate 3-phosphate aromatic amino acid synthesis

Shikimate 3-phosphate with phosphoenolpyruvate

Shikimate accumulation

Shikimate biosynthesis

Shikimate biosynthetic pathway

Shikimate dehydrogenase

Shikimate dehydrogenase, activity

Shikimate dehydrogenase, aromatic amino

Shikimate dehydrogenase, aromatic amino acid biosynthesis

Shikimate dehydrogenase, aromatic amino acid synthesis

Shikimate dehydrogenases

Shikimate hydroxycinnamoyltransferase

Shikimate kinase

Shikimate kinase Shikimic acid

Shikimate kinase synthesis

Shikimate kinase, aromatic amino acid

Shikimate pathway

Shikimate pathway Shikimic acid

Shikimate pathway amino acid synthesis

Shikimate pathway common branch

Shikimate pathway enzymes

Shikimate pathway evidence

Shikimate pathway pigments from

Shikimate pathway regulation

Shikimate pathway scheme

Shikimate pathway targets

Shikimate route, phenylalanine

Shikimate-3-phosphate

Shikimate-chorismate pathway

Shikimate-derived compounds

Shikimate-malonate pathway

Shikimate/arogenate pathway

Shikimates

Shikimic

Shikimic

Shikimic 4,5-methylene

Shikimic Acid to Aromatic Amino Acids

Shikimic acid

Shikimic acid 2.3] Sigmatropic rearrangements

Shikimic acid 5-enolpyruvyl-3-phosphate

Shikimic acid Oseltamivir phosphate

Shikimic acid VOLUME

Shikimic acid antibiotics

Shikimic acid antitumoral activity

Shikimic acid biosynthesis

Shikimic acid biosynthetic

Shikimic acid biosynthetic intermediates

Shikimic acid configuration

Shikimic acid dehydrogenase

Shikimic acid derivatives

Shikimic acid formation

Shikimic acid isolation

Shikimic acid labeled

Shikimic acid metabolism

Shikimic acid pathway

Shikimic acid pathway Claisen rearrangement

Shikimic acid pathway lignins

Shikimic acid pathways, natural products originating from

Shikimic acid phosphate

Shikimic acid route

Shikimic acid structure

Shikimic acid synthesis

Shikimic acid synthetase

Shikimic acid via cyclofunctionalization of cycloalkene

Shikimic acid via cyclohexadienyl complexes

Shikimic acid, conformation

Shikimic acid-derived phenols

Shikimic add

Shikimic dehydrogenase

Shikimic dihydro

Shikimic path

Shikimic pathway

The shikimate pathway

The shikimic acid pathway

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