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8.2 Shikimic Acid Pathway

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8.2 Shikimic Acid Pathway CHAPTER 8 © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FORAromatic SALE OR DISTRIBUTION and NOT FOR SALE OR DISTRIBUTION Phenolic Compounds © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION CHAPTER OUTLINE Overview Synthesis and Properties of Polyketides 8.1 8.5 Synthesis of Chalcones © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC 8.2 Shikimic Acid Pathway Synthesis of Flavanones and Derivatives NOT FOR SALE ORPhenylalanine DISTRIBUTION and Tyrosine Synthesis NOT FOR SALESynthesis OR DISTRIBUTION and Properties of Flavones Tryptophan Synthesis Synthesis and Properties of Anthocyanidins Synthesis and Properties of Isofl avonoids Phenylpropanoid Pathway 8.3 Examples of Other Plant Polyketide Synthases Synthesis of Trans-Cinnamic Acid Synthesis and Activity of Coumarins Lignin Synthesis Polymerization© Jonesof Monolignols & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC Genetic EngineeringNOT FOR of Lignin SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION Natural Products Derived from the 8.4 Phenylpropanoid Pathway Natural Products from Monolignols © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION 119 © Jones & Bartlett Learning, LLC. NOT FOR SALE OR DISTRIBUTION. 8.1 Overview of lignin precursors and is considered a primary © Jones & Bartlett Learning, LLC © Jones & metabolicBartlett Learning,pathway in terrestrialLLC plants. Cou- NOT FOR SALE OR DISTRIBUTIONPlants are autotrophic organisms andNOT must FOR SALEmaroyl-CoA OR DISTRIBUTIONis also the initial compound for a synthesize all their metabolites from the inter- variety of natural products, including flavonoid mediates of the C-3 cycle and other pathways synthesis. of primary carbon and nitrogen metabolism. Flavonoids are found in most plants and This includes the 20 common amino acids used give rise to colored compounds such as antho- in protein© Jones synthesis. & BartlettMany of these Learning, amino acids LLC cyanins. They function© Jones to protect & Bartlett plants from Learning, LLC are synthesizedNOT FOR directly SALE from OR precursors DISTRIBUTION derived intense light and ultravioletNOT FOR (UV) SALE radiation OR and DISTRIBUTION from primary metabolism. For example, the can act as antioxidants. A vast number of addi- amino acid glutamic acid is produced in a single tional natural products are synthesized from reaction: transfer of an amino group to 2-oxo- the aromatic amino acids and their precursors. glutarate (␣-ketoglutaric acid), an intermediate Only a small number of these are presented in © Jonesin & the Bartlett citric acid Learning, cycle. Synthesis LLC of the aromatic this© chapter. Jones & Bartlett Learning, LLC NOT FORamino SALE acids, OR phenylalanine, DISTRIBUTION tyrosine, and tryp- NOT FOR SALE OR DISTRIBUTION tophan, is more complex. In addition to their 8.2 Shikimic Acid Pathway function in protein synthesis, most amino acids serve as precursors for the synthesis of other All three aromatic amino acids are derived from metabolites. This is especially true for phen- intermediates of the same series of reactions, the © Jones & Bartlett Learning,ylalanine, whichLLC is the precursor for the© phen-Jones & shikimicBartlett acid Learning, pathway. Synthesis LLC starts with ery- NOT FOR SALE OR DISTRIBUTIONylpropanoid pathway. Removal of theNOT amino FOR SALEthrose-4-phosphate OR DISTRIBUTION and phosphoenolpyruvic group from phenylalanine yields trans-cinnamic acid (PEP). The pathway is named after the first acid followed by addition of an OH and coen- intermediate that is unique to aromatic amino zyme A, which produces p-coumaroyl-CoA. acid synthesis, shikimic acid. The reactions in This key intermediate is essential in synthesis this pathway are similar in plants, fungi, and bac- © Jones & Bartlett Learning, LLC teria but are absent© in Jones animals. & The Bartlett component Learning, LLC NOT FOR SALE OR DISTRIBUTION enzymes are homologousNOT FORin all these SALE kingdoms. OR DISTRIBUTION Phosphoenol pyruvate + Erythrose-4-phosphate In plants, the enzymes are found in plastids and are presumably all soluble in the stroma. The genes for these enzymes are encoded in the O O– nucleus. An overview of the pathway is shown © Jones &C Bartlett Learning, LLC in ©FIGURE Jones 8.1. In & addition Bartlett to Learning, the three aromatic LLC NOT FOR SALE OR DISTRIBUTION aminoNOT acids, FOR the SALE intermediates OR DISTRIBUTION of the shikimic Phenolics acid pathway are also used in the synthesis of a variety of other metabolites, including the plant HO OH hormone salicylic acid, vitamins such as folic OH acid, and a number of species-specific natural Shikimic acid © Jones & Bartlett Learning, LLC © Jones & products.Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALEThe ORerythrose-4-phosphate DISTRIBUTION precursor is an intermediate in the C-3 cycle and the pentose O O– phosphate pathway in the chloroplast stroma Salicylic acid C (see Chapters 2 and 3). PEP is an intermedi- Benzoic acid ate in glycolysis and may be imported into H C ©2 JonesO & Bartlett Learning,Volatiles LLC chloroplasts. Alternatively,© Jones it can& Bartlett be a product Learning, LLC Quinones (rings) of chloroplast pyruvate metabolism via pyru- ONOT FOR− SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION OH O vate kinase and pyruvate, Pi dikinase. The first Para aminobenzoic acid reaction in the pathway is an aldol condensa- Chorismic acid (folic acid precursor) tion that results in the synthesis of a 7-carbon O ketose, 3-deoxy-arabino-heptulosonic acid- O O © Jones & Bartlett Learning, LLC 7-phosphate© Jones &(DAHP), Bartlett shown Learning, in FIGURE LLC 8.2. + CH C O− + CH C O− H N NOT FOR SALE+ OR CDISTRIBUTIONO− 3 NOT FOR SALE OR DISTRIBUTION H3N CH H3N CH2 CH2 H C 2 FIGURE 8.1 Simplifi ed overview of the shikimic acid pathway. This diagram highlights the main intermediates and products of the shikimic acid pathway. The precursors are phosphoenolpyruvate (PEP) and erythrose-4-phosphate. © JonesHN & Bartlett Learning, LLC Shikimic© Jones acid and & chorismicBartlett acid Learning, are key intermediates. LLC These intermediates OH can be removed from the pathway and used to synthesize a variety of additional NOT FORTryptophan SALE OR DISTRIBUTIONPhenylalanine Tyrosine phenolicNOT FORcompounds. SALE OR DISTRIBUTION 120 CHAPTER 8 Aromatic and Phenolic Compounds © Jones & Bartlett Learning, LLC. NOT FOR SALE OR DISTRIBUTION. H+ FIGURE 8.2 Synthesis of 3-deoxy-arabino- © Jones & Bartlett Learning, LLC O– © Jones &heptulosonic Bartlett acid-7-phosphate Learning, (DAHP).LLC O NOT FORThe SALE DAHP synthaseOR DISTRIBUTION catalyzes an aldol-type NOT FOR SALEO OR DISTRIBUTIONH C condensation. The phosphate is removed H2C O C CH from PEP, and its methylene carbon then –O H C O P C C forms a bond with the carbonyl carbon of – H2 OH O PEP erythrose-4-phosphate. –O OH O O P Erythrose-4-P © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE– OOR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION OH O O© Jones & HBartlett Learning, LLC © Jones & Bartlett Learning, LLC O C6 C – – 7 H CH 3 O O NOT FOR SALE OR4 DISTRIBUTION2 + Pi NOT FOR SALE OR DISTRIBUTION P C C5 C C 1 H2 OH H2 –O OH O 3-Deoxy-arabino-heptulosonic acid-7-P © Jones & Bartlett Learning, LLC © Jones & Bartlett Learning, LLC NOT FOR SALE OR DISTRIBUTION NOT FOR SALE OR DISTRIBUTION DAHP synthases in plants and bacteria show Dehydroquinic acid is the substrate for a only about 20% amino acid identity. The plant dehydratase that catalyzes removal of water and enzyme, however, complements bacterial mu- introduces a double bond into the ring. This is tants lacking this synthase. The bacterial enzyme followed by reduction of the ketone to an alco- exhibits feedback inhibition© Jones by & the Bartlett aromatic Learning, hol forming LLC shikimic acid, the first ©unique Jones inter- & Bartlett Learning, LLC amino acid end products,NOT phenylalanineFOR SALE OR and DISTRIBUTIONmediate (FIGURE 8.4). In some plants,NOT shikimic FOR SALE OR DISTRIBUTION tyrosine. This does not appear to be true of the acid is the starting material for the synthesis of plant synthases. Expression of different iso- a variety of phenolic natural products. The most zymes of DAHP synthase in plants, however, common are the water-soluble gallotannins, is influenced by environmental factors such as which are complexes of phenolics with sugars, high ©light Jones intensity & Bartlett or wounding Learning, and the pres-LLC usually glucose. Plants© Jones make &these Bartlett compounds Learning, LLC ence NOTof hormones, FOR SALE gibberellic OR acid DISTRIBUTION and jasmonic to protect their tissuesNOT from FOR UV SALE damage OR and DISTRIBUTION to acid. The intermediates and end products of the deter herbivores. Tannins can bind irreversibly
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