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Pathways to Terpenes Classes Different Biosynthetic Leading the of

TopolWish33
28.11.2018

Content:

  • Pathways to Terpenes Classes Different Biosynthetic Leading the of
  • 27.5: Terpenoids
  • More From NC State News
  • In contrast to other classes of terpenes that vary greatly in structure and molecular size, the . limiting enzyme of the mevalonate pathway of cholesterol synthesis. Subsequent steps lead to the important C5 building blocks IPP and DMAPP. In contrast to other classes of terpenes that vary greatly in structure and molecular size, the enzymes involved in the pathway have been isolated and studied. Subsequent steps lead to the important C5 building blocks IPP and DMAPP. Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, Terpenes are derived biosynthetically from units of isopentenyl pyrophosphate. One of the intermediates in this pathway is mevalonic acid.

    Pathways to Terpenes Classes Different Biosynthetic Leading the of

    In the case of the triterpene lanosterol we see an interesting deviation from the isoprene rule. This thirty carbon compound is clearly a terpene, and four of the six isopentane units can be identified.

    However, the ten carbons in center of the molecule cannot be dissected in this manner. Evidence exists that the two methyl groups circled in magenta and light blue have moved from their original isoprenoid locations marked by small circles of the same color to their present location.

    This rearrangement is described in the biosynthesis section. Similar alkyl group rearrangements account for other terpenes that do not strictly follow the isoprene rule. Polymeric isoprenoid hydrocarbons have also been identified. Rubber is undoubtedly the best known and most widely used compound of this kind.

    It occurs as a colloidal suspension called latex in a number of plants, ranging from the dandelion to the rubber tree Hevea brasiliensis. Bromine, hydrogen chloride and hydrogen all add with a stoichiometry of one molar equivalent per isoprene unit.

    Pyrolysis of rubber produces the diene isoprene along with other products. The double bonds in rubber all have a Z-configuration, which causes this macromolecule to adopt a kinked or coiled conformation. This is reflected in the physical properties of rubber. Despite its high molecular weight about one million , crude latex rubber is a soft, sticky, elastic substance.

    Chemical modification of this material is normal for commercial applications. Gutta-percha structure above is a naturally occurring E-isomer of rubber. Here the hydrocarbon chains adopt a uniform zig-zag or rod like conformation, which produces a more rigid and tough substance. Uses of gutta-percha include electrical insulation and the covering of golf balls.

    While we can identify isoprene units within a terpenoid structure and use that in its classification, the building block for terpenoid synthesis in nature is isopentenyl diphosphate formerly called isopentenyl pyrophosphate and abbreviated IPP.

    There are two major routes to the synthesis of IPP; namely 1 the mevalonate pathway and 2 the 1-deoxyxylulose pathway. Step 1 - Claisen Condensation.

    An initial trans-thioesterase process transfers the acetyl group of the first acetyl CoA to an enzymatic cysteine Reaction 1. In the Claisen condensation phase of the reaction, the alpha-carbon of a second acetyl CoA is deprotonated, forming an enolate Reaction 2. The enolate carbon attacks the electrophilic thioester carbon, forming a tetrahedral intermediate Reaction 3 which quickly collapses to expel the cysteine thiol Reaction 4 and produce acetoacetyl CoA.

    Step 2 - Aldol Condensation. Acetyl CoA then reacts with the acetoacetyl CoA in an aldol-like addition. Step 3 - Reduction of the Thioester. The thioester is reduced first to an aldehyde, then to a primary alcohol by two equivalents of NADPH producing R -mevalonate. The enzyme catalyzing this reaction is the target of the statin family of cholesterol-lowering drugs. Step 4 - Mevalonate Phosphorylation. Step 5 - Decarboxylation. Finally isopentenyl diphosphate IPP , the 'building block' for all isoprenoid compounds, is formed from a decarboxylation-elimination reaction.

    The electrophilic double bond isomerization catalyzed by IPP isomerase is a highly reversible reaction, with an equilibrium IPP: DMAPP ratio of about 6: In the next step of isoprenoid biosynthesis, the two five-carbon isomers condense to form a carbon isoprenoid product called geranyl diphosphate GPP. The first step is ionization of the electrophile - in other words, the leaving group departs and a carbocation intermediate is formed. In this case, the pyrophosphate group on DMAPP is the leaving group, and the electrophilic species is the resulting allylic carbocation.

    In the condensation addition step, the C 3 -C 4 double bond in IPP attacks the positively-charged C 1 of DMAPP, resulting in a new carbon-carbon bond and a second carbocation intermediate, this time at a tertiary carbon. In the elimination phase, proton abstraction leads to re-establishment of a double bond in the GPP product. Notice that the enzyme specifically takes the pro-R proton in this step. To continue the chain elongation process, another IPP molecule can then condense, in a very similar reaction, with C 1 of geranyl diphosphate to form a carbon product called farnesyl diphosphate FPP.

    How do we know that these are indeed S N 1-like mechanisms with carbocation intermediates, rather than concerted S N 2-like mechanisms? First of all, recall that the question of whether a substitution is dissociative S N 1-like or associative S N 2-like is not always clear-cut - it could be somewhere in between, like the protein prenyltransferase reaction.

    The protein prenyltransferase reaction and the isoprenoid chain elongation reactions are very similar: This difference in the identity of the nucleophilic species would lead one to predict that the chain elongation reaction has more S N 1-like character than the protein prenylation reaction. A thiolate is a very powerful nucleophile, and thus is able to push the pyrophosphate leaving group off, implying some degree of S N 2 character. The electrons in a pi bond, in contrast, are only weakly nucleophilic, and thus need to be pulled in by a powerful electrophile - ie.

    So it makes perfect sense that the chain elongation reaction should more S N 1-like than S N 2-like. Is this in fact the case? Similar alkyl group rearrangements account for other terpenes that do not strictly follow the isoprene rule. Polymeric isoprenoid hydrocarbons have also been identified. Rubber is undoubtedly the best known and most widely used compound of this kind. It occurs as a colloidal suspension called latex in a number of plants, ranging from the dandelion to the rubber tree Hevea brasiliensis.

    Bromine, hydrogen chloride and hydrogen all add with a stoichiometry of one molar equivalent per isoprene unit. Pyrolysis of rubber produces the diene isoprene along with other products. The double bonds in rubber all have a Z-configuration, which causes this macromolecule to adopt a kinked or coiled conformation. This is reflected in the physical properties of rubber. Despite its high molecular weight about one million , crude latex rubber is a soft, sticky, elastic substance.

    Chemical modification of this material is normal for commercial applications. Gutta-percha structure above is a naturally occurring E-isomer of rubber. Here the hydrocarbon chains adopt a uniform zig-zag or rod like conformation, which produces a more rigid and tough substance. Uses of gutta-percha include electrical insulation and the covering of golf balls. While we can identify isoprene units within a terpenoid structure and use that in its classification, the building block for terpenoid synthesis in nature is isopentenyl diphosphate formerly called isopentenyl pyrophosphate and abbreviated IPP.

    There are two major routes to the synthesis of IPP; namely 1 the mevalonate pathway and 2 the 1-deoxyxylulose pathway. Step 1 - Claisen Condensation. An initial trans-thioesterase process transfers the acetyl group of the first acetyl CoA to an enzymatic cysteine Reaction 1.

    In the Claisen condensation phase of the reaction, the alpha-carbon of a second acetyl CoA is deprotonated, forming an enolate Reaction 2. The enolate carbon attacks the electrophilic thioester carbon, forming a tetrahedral intermediate Reaction 3 which quickly collapses to expel the cysteine thiol Reaction 4 and produce acetoacetyl CoA.

    Step 2 - Aldol Condensation. Acetyl CoA then reacts with the acetoacetyl CoA in an aldol-like addition. Step 3 - Reduction of the Thioester. The thioester is reduced first to an aldehyde, then to a primary alcohol by two equivalents of NADPH producing R -mevalonate. The enzyme catalyzing this reaction is the target of the statin family of cholesterol-lowering drugs.

    Step 4 - Mevalonate Phosphorylation. Step 5 - Decarboxylation. Finally isopentenyl diphosphate IPP , the 'building block' for all isoprenoid compounds, is formed from a decarboxylation-elimination reaction. The electrophilic double bond isomerization catalyzed by IPP isomerase is a highly reversible reaction, with an equilibrium IPP: DMAPP ratio of about 6: In the next step of isoprenoid biosynthesis, the two five-carbon isomers condense to form a carbon isoprenoid product called geranyl diphosphate GPP.

    The first step is ionization of the electrophile - in other words, the leaving group departs and a carbocation intermediate is formed. In this case, the pyrophosphate group on DMAPP is the leaving group, and the electrophilic species is the resulting allylic carbocation. In the condensation addition step, the C 3 -C 4 double bond in IPP attacks the positively-charged C 1 of DMAPP, resulting in a new carbon-carbon bond and a second carbocation intermediate, this time at a tertiary carbon.

    In the elimination phase, proton abstraction leads to re-establishment of a double bond in the GPP product. Notice that the enzyme specifically takes the pro-R proton in this step. To continue the chain elongation process, another IPP molecule can then condense, in a very similar reaction, with C 1 of geranyl diphosphate to form a carbon product called farnesyl diphosphate FPP. How do we know that these are indeed S N 1-like mechanisms with carbocation intermediates, rather than concerted S N 2-like mechanisms?

    First of all, recall that the question of whether a substitution is dissociative S N 1-like or associative S N 2-like is not always clear-cut - it could be somewhere in between, like the protein prenyltransferase reaction. The protein prenyltransferase reaction and the isoprenoid chain elongation reactions are very similar: This difference in the identity of the nucleophilic species would lead one to predict that the chain elongation reaction has more S N 1-like character than the protein prenylation reaction.

    A thiolate is a very powerful nucleophile, and thus is able to push the pyrophosphate leaving group off, implying some degree of S N 2 character. The electrons in a pi bond, in contrast, are only weakly nucleophilic, and thus need to be pulled in by a powerful electrophile - ie. So it makes perfect sense that the chain elongation reaction should more S N 1-like than S N 2-like. Is this in fact the case? We know how to answer this question experimentally - just run the reaction with fluorinated DMAPP or GPP substrates and observe how much the fluorines slow things down.

    If the reaction is S N 1-like, the electron-withdrawing fluorines should destabilize the allylic carbocation intermediate and thus slow the reaction down considerably. If the mechanism is S N 2-like, the fluorine substitutions should not have a noticeable effect, because a carbocation intermediate would not be formed. When this experiment was performed with FPP synthase, the results were dramatic: These results strongly suggest indicate the formation of a carbocation intermediate in an S N 1-like displacement.

    27.5: Terpenoids

    Biosynthesis of Isoprenoids. David Wang's Natural Products Class. Terpene plants for many different purposes — as fragrances . The evidence now indicates that the biosynthetic pathways for the . GPP leads initially to the tertiary. -Terpenes are an enormous class of natural products spanning well over 30, -There are 2 biosynthetic pathways for the production of IPP and DMAPP, the leads to many different carbocyclic skeletons, which are often further oxidized. The condensation of acetyl CoA three units leads to the synthesis of Another part of terpenoid biosynthetic pathway starts in plastid by the Plant genomes appear to encode various farnesyl diphosphate The class of triterpenes includes sterols and triterpenoids, which.

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    Comments

    mthlcr11

    Biosynthesis of Isoprenoids. David Wang's Natural Products Class. Terpene plants for many different purposes — as fragrances . The evidence now indicates that the biosynthetic pathways for the . GPP leads initially to the tertiary.

    alexkov11

    -Terpenes are an enormous class of natural products spanning well over 30, -There are 2 biosynthetic pathways for the production of IPP and DMAPP, the leads to many different carbocyclic skeletons, which are often further oxidized.

    sawyer

    The condensation of acetyl CoA three units leads to the synthesis of Another part of terpenoid biosynthetic pathway starts in plastid by the Plant genomes appear to encode various farnesyl diphosphate The class of triterpenes includes sterols and triterpenoids, which.

    fartuna700

    structural diversity and biochemical specificity making them leading scaffolds for drug of terpenoids, their different classes and biosynthesis shedding Two distinct biosynthetic pathways for the formation of these universal.

    atis2006

    few well-studied fungal biosynthetic pathways, the majority of genes and biosyn- .. The different classes of characterized terpenoid natural products can be distin - . This leads to the formation of an allylic cation that triggers.

    Sn3kle

    2 Core Terpenoid Biosynthetic Pathways and Their Regulation. Reduced. expression of HMGR1 in transgenic plants causes a severe decrease of root nod- . ulation []. . Different classes of homodimeric and heterodi/.

    antip

    The mevalonate pathway is of biomedical interest in certain types of cancer as in biosynthetic pathways leading to sterols, terpenes, carotenoids, and other.

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