26.7 Terpenes: The Isoprene Rule
|
|
|
- Augustine Norman
- 7 years ago
- Views:
Transcription
1 26.7 Terpenes: The Isoprene Rule
2 Terpenes Terpenes are natural products that are structurally related to isoprene. CH 3 H 2 C C CH CH 2 or Isoprene (2-methyl methyl-1,3-butadiene)
3 Terpenes Myrcene (isolated from oil of bayberry) is a typical terpene. CH 3 C CH 3 CHCH 2 CH 2 CCH or CH 2 CH 2
4 The Isoprene Unit An isoprene unit is the carbon skeleton of isoprene (ignoring the double bonds) Myrcene contains two isoprene units.
5 The Isoprene Unit The isoprene units of myrcene are joined "head- to-tail." tail." head tail tail head
6 Table 26.2 Classification of Terpenes Class Number of carbon atoms Monoterpene 10 Sesquiterpene 15 Diterpene 20 Sesterpene 25 Triterpene 30 Tetraterpene 40
7 Figure 26.6 Representative Monoterpenes H H α-phellandrene (eucalyptus) Menthol (peppermint) Citral (lemon grass)
8 Figure 26.6 Representative Monoterpenes H H α-phellandrene (eucalyptus) Menthol (peppermint) Citral (lemon grass)
9 Figure 26.6 Representative Monoterpenes α-phellandrene (eucalyptus) Menthol (peppermint) Citral (lemon grass)
10 Figure 26.6 Representative Sesquiterpenes H α-selinene (celery)
11 Figure 26.6 Representative Sesquiterpenes H α-selinene (celery)
12 Figure 26.6 Representative Sesquiterpenes α-selinene (celery)
13 Figure 26.6 Representative Diterpenes H Vitamin A
14 Figure 26.6 Representative Diterpenes H Vitamin A
15 Figure 26.6 Representative Diterpenes Vitamin A
16 Figure 26.6 Representative Triterpene tail-to to-tail tail linkage of isoprene units Squalene (shark liver oil)
17 26.8 Isopentenyl Pyrophosphate: The Biological Isoprene Unit
18 The Biological Isoprene Unit The isoprene units in terpenes do not come from isoprene. They come from isopentenyl pyrophosphate. Isopentenyl pyrophosphate (5 carbons) comes from acetate (2 carbons) via mevalonate (6 carbons).
19 The Biological Isoprene Unit CH 3 3CH 3 CH HCCH 2 CCH 2 CH 2 H H CH 3 Mevalonic acid H 2 C CCH 2 CH 2 PPH Isopentenyl pyrophosphate
20 Isopentenyl Pyrophosphate CH 3 H 2 C CCH 2 CH 2 PPH or PP Isopentenyl pyrophosphate
21 Isopentenyl and Dimethylallyl Pyrophosphate Isopentenyl pyrophosphate is interconvertible with 2-methylallyl pyrophosphate. PP Isopentenyl pyrophosphate PP Dimethylallyl pyrophosphate Dimethylallyl pyrophosphate has a leaving group (pyrophosphate) at an allylic carbon; it is reactive toward nucleophilic substitution at this position.
22 26.9 Carbon-Carbon Bond Formation in Terpene Biosynthesis
23 Carbon-Carbon Bond Formation PP + PP The key process involves the double bond of isopentenyl pyrophosphate acting as a nucleophile toward the allylic carbon of dimethylallyl pyrophosphate.
24 Carbon-Carbon Bond Formation PP + PP PP + PP
25 After C C C C Bond Formation... The carbocation can lose a proton to give a double bond. + PP
26 After C C C C Bond Formation... PP The carbocation can lose a proton to give a double bond. H + + PP
27 After C C C C Bond Formation... PP This compound is called geranyl pyrophosphate. It can undergo hydrolysis of its pyrophosphate to give geraniol (rose oil).
28 After C C C C Bond Formation... PP H 2 Geraniol H
29 From 10 Carbons to 15 PP + PP Geranyl pyrophosphate + PP
30 From 10 Carbons to 15 PP H + + PP
31 From 10 Carbons to 15 This compound is called farnesyl pyrophosphate. PP Hydrolysis of the pyrophosphate ester gives the alcohol farnesol (Figure 26.6).
32 From 15 Carbons to 20 PP PP Farnesyl pyrophosphate is extended by another isoprene unit by reaction with isopentenyl pyrophosphate.
33 Cyclization Rings form by intramolecular carbon-carbon bond formation. + PP PP E double bond Z double bond
34 Limonene H + H + H 2 α-terpineol
35 Bicyclic Terpenes α-pinene β-pinene
36 26.10 The Pathway from Acetate to Isopentenyl Pyrophosphate
37 Recall CH 3 3CH 3 CH HCCH 2 CCH 2 CH 2 H H CH 3 Mevalonic acid H 2 C CCH 2 CH 2 PPH Isopentenyl pyrophosphate
38 Biosynthesis of Mevalonic Acid In a sequence analogous to the early steps of fatty acid biosynthesis, acetyl coenzyme A is converted to S-acetoacetyl coenzyme A. CH 3 CCH 2 CSCoA S-Acetoacetyl coenzyme A
39 Biosynthesis of Mevalonic Acid CH 3 CCH 2 CSCoA + CH 3 CSCoA In the next step, S-acetoacetyl S coenzyme A reacts with acetyl coenzyme A. Nucleophilic addition of acetyl coenzyme A (probably via its enol) to the ketone carbonyl of S-acetoacetyl coenzyme A occurs.
40 Biosynthesis of Mevalonic Acid CH 3 CCH 2 CSCoA + CH 3 CSCoA H CH 3 CCHCH 2 CSCoA CH 2 CH
41 Biosynthesis of Mevalonic Acid Next, the acyl coenzyme A function is reduced. The product of this reduction is mevalonic acid. H CH 3 CCHCH 2 CSCoA CH 2 CH
42 H CH 3 CCHCH 2 CH 2 H CH 2 CH Mevalonic acid H CH 3 CCHCH 2 CSCoA CH 2 CH
43 Conversion of Mevalonic Acid to Isopentenyl Pyrophosphate H CH 3 CCH 2 CH 2 H CH 2 CH 2 P 3 CH 3 CCH 2 CH 2 PP CH 2 CH The two hydroxyl groups of mevalonic acid undergo phosphorylation.
44 Conversion of Mevalonic Acid to Isopentenyl Pyrophosphate 3 P 3 CH 3 CCH 2 CH 2 PP CH 2 C 2 P 3 CH 3 CCH 2 CH 2 PP CH 2 C Phosphorylation is followed by a novel elimination involving loss of C 2 and P 3 4.
45 Conversion of Mevalonic Acid to Isopentenyl Pyrophosphate CH 3 CCH 2 CH 2 PP CH 2 The product of this elimination is isopentenyl pyrophosphate.
46 Biosynthetic pathway is based on experiments with 14 C-labeled acetate CH 3 CH 3 CH HCCH 2 CCH 2 CH 2 H CH 3 H Mevalonic acid H 2 C CCH 2 CH 2 PPH Isopentenyl pyrophosphate
47 Biosynthetic pathway is based on experiments with 14 C-labeled acetate Citronellal biosynthesized using 14 C-labeled acetate as the carbon source had the labeled carbons in the positions indicated. CH 3 CH 3 CH H 2 C CCH 2 CH 2 PPH H
Steam Distillation of Lemongrass Oil
I. Introduction Steam Distillation of Lemongrass Oil When a mixture of cyclohexane and toluene is distilled, the boiling point of these two miscible liquids is between the boiling points of each of the
Chapter 22 Carbonyl Alpha-Substitution Reactions
John E. McMurry www.cengage.com/chemistry/mcmurry Chapter 22 Carbonyl Alpha-Substitution Reactions The α Position The carbon next to the carbonyl group is designated as being in the α position Electrophilic
4/18/2011. 9.8 Substituent Effects in Electrophilic Substitutions. Substituent Effects in Electrophilic Substitutions
9.8 Substituent effects in the electrophilic substitution of an aromatic ring Substituents affect the reactivity of the aromatic ring Some substituents activate the ring, making it more reactive than benzene
Introduction to Biodiesel Chemistry Terms and Background Information
Introduction to Biodiesel Chemistry Terms and Background Information Basic rganic Chemistry rganic chemistry is the branch of chemistry that deals with organic compounds. rganic compounds are compounds
Ch17_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
Ch17_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Which molecule is a carboxylic acid? A) 1) B) C) D) E) CH3 CH2 CH2 NH2 2) Which molecule
Regulation of cholesterol synthesis pathway. Cholesterol Synthesis. Cholesterol biosynthesis. Regulation of HMG CoA reductase activity
Cholesterol Synthesis Main function: ation of steroid nucleus Substrate: cytoplasmic acetyl CoA Endproduct: cholesterol Location: cytoplasm Regulation of cholesterol synthesis pathway HMG CoA reductase
Organic Functional Groups Chapter 7. Alcohols, Ethers and More
Organic Functional Groups Chapter 7 Alcohols, Ethers and More 1 What do you do when you are in Pain? What do you do when you are in a lot of pain? 2 Functional Groups A functional group is an atom, groups
The Citric Acid Cycle
The itric Acid ycle February 14, 2003 Bryant Miles I. itrate Synthase + 3 SoA The first reaction of the citric acid cycle is the condensation of acetyloa and oxaloacetate to form citrate and oas. The enzyme
Reactions of Fats and Fatty Acids
Reactions of Fats and Fatty Acids Outline Fats and Oils Fatty Acid Biosynthesis Biodiesel Homework We hear quite a lot about the place of fats and oils in human nutrition. Foods high in fat are at the
EXPERIMENT 5: DIPEPTIDE RESEARCH PROJECT
EXPERIMENT 5: DIPEPTIDE RESEARCH PROJECT Pre-Lab Questions: None. 64 I. Background Information DIPEPTIDE RESEARCH PROJECT Methods developed by organic chemists for the synthesis of biopolymers have had
Unsaturated and Odd-Chain Fatty Acid Catabolism
Unsaturated and dd-hain Fatty Acid atabolism March 24, 2003 Bryant Miles The complete oxidation of saturated fatty acids containing an even number of carbon atoms is accomplished by the β-oxidation pathway.
But in organic terms: Oxidation: loss of H 2 ; addition of O or O 2 ; addition of X 2 (halogens).
Reactions of Alcohols Alcohols are versatile organic compounds since they undergo a wide variety of transformations the majority of which are either oxidation or reduction type reactions. Normally: Oxidation
The Structure and Function of Macromolecules: Carbohydrates, Lipids & Phospholipids
The Structure and Function of Macromolecules: Carbohydrates, Lipids & Phospholipids The FOUR Classes of Large Biomolecules All living things are made up of four classes of large biological molecules: Carbohydrates
Carboxylic Acid Derivatives and Nitriles
Carboxylic Acid Derivatives and itriles Carboxylic Acid Derivatives: There are really only four things to worry about under this heading; acid chlorides, anhydrides, esters and amides. We ll start with
17.5 ALLYLIC AND BENZYLIC OXIDATION
17.5 ALLYLI AND BENZYLI XIDATIN 803 Nuc d d Nuc d 2 3 2 overlap of 2p orbitals X d no p-orbital overlap X d (a) (b) Figure 17.2 Transition states for N 2 reactions at (a) an allylic carbon and (b) a nonallylic
Alcohols An alcohol contains a hydroxyl group ( OH) attached to a carbon chain. A phenol contains a hydroxyl group ( OH) attached to a benzene ring.
Chapter : rganic Compounds with xygen Alcohols, Ethers Alcohols An alcohol contains a hydroxyl group ( H) attached to a carbon chain. A phenol contains a hydroxyl group ( H) attached to a benzene ring.
Waxes. From the head of sperm whales Structural material of beehives Coating on the leaves of Brazilian palm. Fats and Oils
Lipids Lipids are organic compounds that contain hydrocarbons which are the foundation for the structure and function of living cells. Lipids are non polar so they are soluble in nonpolar environments
Chapter 10. Conjugation in Alkadienes and Allylic Systems. Class Notes. B. The allyl group is both a common name and an accepted IUPAC name
Chapter 10 Conjugation in Alkadienes and Allylic Systems Chapter 10 suggested problems: I. The allyl group Class Notes A. B. The allyl group is both a common name and an accepted IUPAC name 1. Allyl alcohol
Fatty Acids carboxylic acids
Triglycerides (TG) should actually be called triacylglycerols (TAG). TG or TAG are molecules with a glycerol (a carbohydrate) backbone to which are attached three acyl groups. They represent a concentrated
Bioenergetics. Free Energy Change
Bioenergetics Energy is the capacity or ability to do work All organisms need a constant supply of energy for functions such as motion, transport across membrane barriers, synthesis of biomolecules, information
Aldehydes can react with alcohols to form hemiacetals. 340 14. Nucleophilic substitution at C=O with loss of carbonyl oxygen
340 14. Nucleophilic substitution at C= with loss of carbonyl oxygen Ph In Chapter 13 we saw this way of making a reaction go faster by raising the energy of the starting material. We also saw that the
Resonance Structures Arrow Pushing Practice
Resonance Structures Arrow Pushing Practice The following is a collection of ions and neutral molecules for which several resonance structures can be drawn. For the ions, the charges can be delocalized
Chapter 5: The Structure and Function of Large Biological Molecules
Name Period Concept 5.1 Macromolecules are polymers, built from monomers 1. The large molecules of all living things fall into just four main classes. Name them. 2. Circle the three classes that are called
1. Explain the difference between fermentation and cellular respiration.
: Harvesting Chemical Energy Name Period Overview: Before getting involved with the details of cellular respiration and photosynthesis, take a second to look at the big picture. Photosynthesis and cellular
CHEM 121. Chapter 19, Name: Date:
CHEM 121. Chapter 19, Name: Date: 1. A lipid is any substance of biochemical origin that is A) soluble in water but insoluble in nonpolar solvents B) insoluble in both water and nonpolar solvents C) insoluble
UNIT (9) CARBOXYLIC ACIDS, ESTERS, AMINES, AND AMIDES
UNIT (9) CARBXYLIC ACIDS, ESTERS, AMINES, AND AMIDES 9.1 Carboxylic Acids The functional group in carboxylic acids is called the carboxyl group. A carboxyl group is a carbonyl group (C = ) with a hydroxyl
UNIT (11) MOLECULES OF LIFE: LIPIDS AND PROTEINS
UNIT (11) MOLECULES OF LIFE: LIPIDS AND PROTEINS 11.1 Types of Lipids Lipids are also biochemical compounds that contain carbon, hydrogen, and oxygen. But lipids, unlike carbohydrates, share no common
Chapter 6. Alkenes: Structure and Stability
hapter 6. Alkenes: Structure and Stability Steric Acid (saturated fatty acid) Linoleic Acid (unsaturated fatty acid) Degrees of unsaturation saturated hydrocarbon n 2n2 cycloalkane (1 ring) n 2n alkene
Double Bonds. Hydration Rxns. Hydrogenation Rxns. Halogenation. Formation of epoxides. Syn addition of 2 OH. Ozonolysis
Double Bonds What do we do with double bonds? We do addition reactions. In an addition reaction, something is added to both carbons involved in a double bond (or not involved in the double bond, in the
Mass Spec - Fragmentation
Mass Spec - Fragmentation An extremely useful result of EI ionization in particular is a phenomenon known as fragmentation. The radical cation that is produced when an electron is knocked out of a neutral
Assessment Schedule 2013 Chemistry: Demonstrate understanding of the properties of organic compounds (91391)
NCEA Level 3 Chemistry (91391) 2013 page 1 of 8 Assessment Schedule 2013 Chemistry: Demonstrate understanding of the properties of organic compounds (91391) Evidence Statement Q Evidence Achievement Achievement
Chapter 3 Molecules of Cells
Bio 100 Molecules of cells 1 Chapter 3 Molecules of Cells Compounds containing carbon are called organic compounds Molecules such as methane that are only composed of carbon and hydrogen are called hydrocarbons
The Aldol Condensation
The Aldol ondensation Synthesis and Analysis of 2,3,4,5-Tetraphenylcyclopentadienone Yakety Sax Bennie ill theme song TPP eactions of Aldehydes and Ketones ' 1. Nucleophilic Addition. 2. Substitution at
Previous lecture: Today:
Previous lecture: The energy requiring step from substrate to transition state is an energy barrier called the free energy of activation G Transition state is the unstable (10-13 seconds) highest energy
Avg. 16.4 / 25 Stnd. Dev. 8.2
QUIZ TREE Avg. 16.4 / 25 Stnd. Dev. 8.2 xidation of Alcohols with Chromium (VI): Jones xidation 2 Alcohols are oxidized by a solution of chromium trioxide in aqueous acetone (2), in the presence of an
CH 102 Practice Exam 2 PCC-Sylvania
CH 102 Practice Exam 2 PCC-Sylvania True/False Indicate if the statement is true or false. 1.Tertiary alcohols are not easily oxidized. 2.Secondary alcohols can be oxidized to aldehydes. 3.Primary alcohols
AP BIOLOGY CHAPTER 7 Cellular Respiration Outline
AP BIOLOGY CHAPTER 7 Cellular Respiration Outline I. How cells get energy. A. Cellular Respiration 1. Cellular respiration includes the various metabolic pathways that break down carbohydrates and other
Name. Department of Chemistry and Biochemistry SUNY/Oneonta. Chem 322 - Organic Chemistry II Examination #2 - March 14, 2005 ANSWERS
Name INSTRUTINS --- Department of hemistry and Biochemistry SUNY/neonta hem 322 - rganic hemistry II Examination #2 - March 14, 2005 ANSWERS This examination has two parts. Part I is in multiple choice
Chapter 5 Classification of Organic Compounds by Solubility
Chapter 5 Classification of Organic Compounds by Solubility Deductions based upon interpretation of simple solubility tests can be extremely useful in organic structure determination. Both solubility and
21.8 The Citric Acid Cycle
21.8 The Citric Acid Cycle The carbon atoms from the first two stages of catabolism are carried into the third stage as acetyl groups bonded to coenzyme A. Like the phosphoryl groups in ATP molecules,
1 Common Mechanisms in
ommon Mechanisms in Biological hemistry This scheme shows the active site of the enzyme that catalyzes the transamination reaction in the biosynthesis of phenylalanine from chorismate. A mechanistic understanding
Elements in Biological Molecules
Chapter 3: Biological Molecules 1. Carbohydrates 2. Lipids 3. Proteins 4. Nucleic Acids Elements in Biological Molecules Biological macromolecules are made almost entirely of just 6 elements: Carbon (C)
Synthesis of Isopentyl Acetate
Experiment 8 Synthesis of Isopentyl Acetate Objectives To prepare isopentyl acetate from isopentyl alcohol and acetic acid by the Fischer esterification reaction. Introduction Esters are derivatives of
I. Chapter 5 Summary. II. Nucleotides & Nucleic Acids. III. Lipids
I. Chapter 5 Summary A. Simple Sugars (CH 2 O) n : 1. One C contains a carbonyl (C=O) rest contain - 2. Classification by functional group: aldoses & ketoses 3. Classification by number of C's: trioses,
HOMEWORK PROBLEMS: IR SPECTROSCOPY AND 13C NMR. The peak at 1720 indicates a C=O bond (carbonyl). One possibility is acetone:
HMEWRK PRBLEMS: IR SPECTRSCPY AND 13C NMR 1. You find a bottle on the shelf only labeled C 3 H 6. You take an IR spectrum of the compound and find major peaks at 2950, 1720, and 1400 cm -1. Draw a molecule
CHEM 203 Exam 1. KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question.
CHEM 203 Exam 1 KEY Name Multiple Choice Identify the letter of the choice that best completes the statement or answers the question. _D C 1. Which of the following elements is a large percentage of both
CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway
CHEM 322 Organic Chemistry II - Professor Kathleen V. Kilway "Organic Chemistry" by Maitland Jones, 4th edition Chapter 12 Homework: 1, 2, 4, 5, 6, 7, 15, 16, 17, 19, 21, 24, 26, 28, 29, 30, 38, 39, 44,
Unit Vocabulary: o Organic Acid o Alcohol. o Ester o Ether. o Amine o Aldehyde
Unit Vocabulary: Addition rxn Esterification Polymer Alcohol Ether Polymerization Aldehyde Fermentation Primary Alkane Functional group Saponification Alkene Halide (halocarbon) Saturated hydrocarbon Alkyne
Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
Chapter 11 Homework and practice questions Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations SHORT ANSWER Exhibit 11-1 Circle your response in each set below. 1. Circle the least
ALCOHOLS: Properties & Preparation
ALLS: Properties & Preparation General formula: R-, where R is alkyl or substitued alkyl. Ar-: phenol - different properties. Nomenclature 1. ommon names: Name of alkyl group, followed by word alcohol.
INTDUCTIN T LEWIS ACID-BASE CEMISTY DEINITINS Lewis acids and bases are defined in terms of electron pair transfers. A Lewis base is an electron pair donor, and a Lewis acid is an electron pair acceptor.
Copyright 2000-2003 Mark Brandt, Ph.D. 59
The Tricarboxylic Acid Cycle Background (why are eight enzymes necessary?) In principle, acetyl-coa could be converted to carbon dioxide very simply. However, doing so has three potential problems: 1)
(Woods) Chem-131 Lec-19 09-4 Lipids 1. Lipids:
(Woods) Chem-131 Lec-19 09-4 Lipids 1 Lipids Classifying Lipids Triacylglycerols (triglycerides): a storage form of energy not required for immediate use. Phospholipids, p sphingolipids, p and cholesterol
Please read and sign the Honor Code statement below:
CHEM 3311 Exam #1 Name Dr. Minger June 8, 2015 Please read and sign the Honor Code statement below: I pledge that on my honor, as a University of Colorado at Boulder student, I have neither given nor received
1. The functional group present in carboxylic acids is called a A) carbonyl group. B) carboxyl group. C) carboxylate group. D) carbohydroxyl group.
Name: Date: 1. The functional group present in carboxylic acids is called a A) carbonyl group. B) carboxyl group. C) carboxylate group. D) carbohydroxyl group. 2. Which of the following statements concerning
Chapter 16 The Citric Acid Cycle
Chapter 16 The Citric Acid Cycle Multiple Choice Questions 1. Production of acetyl-coa (activated acetate) Page: 603 Difficulty: 2 Ans: A Which of the following is not true of the reaction catalyzed by
Chapter 13 Carboxylic Acids, Esters, Amines, and Amides. Carboxylic Acids. Names and Sources of Some Carboxylic Acids. IUPAC Names
Chapter 13 Carboxylic Acids, Esters, Amines, and Amides 13.1 Carboxylic Acids Carboxylic Acids A carboxylic acid contains a carboxyl group, which is a carbonyl group (C=) attached to a hydroxyl group (
Carbohydrates, proteins and lipids
Carbohydrates, proteins and lipids Chapter 3 MACROMOLECULES Macromolecules: polymers with molecular weights >1,000 Functional groups THE FOUR MACROMOLECULES IN LIFE Molecules in living organisms: proteins,
The Aerobic Fate of Pyruvate
The Aerobic Fate of yruvate February 12, 2003 Bryant Miles I could tell that some of you were not impressed by the mere 2 ATs produced per glucose by glycolysis. The 2 AT s produced are only a small fraction
Chapter 7 Active Reading Guide Cellular Respiration and Fermentation
Name: AP Biology Mr. Croft Chapter 7 Active Reading Guide Cellular Respiration and Fermentation Overview: Before getting involved with the details of cellular respiration and photosynthesis, take a second
NOMENCLATURE OF ORGANIC COMPOUNDS 2010, 2003, 1980, by David A. Katz. All rights reserved.
NMENCLATURE F RGANIC CMPUNDS 2010, 2003, 1980, by David A. Katz. All rights reserved. rganic chemistry is the chemistry of carbon compounds. Carbon has the ability to bond with itself to form long chains
Benzene Benzene is best represented as a resonance hybrid:
Electrophilic Aromatic Substitution (EAS) is a substitution reaction usually involving the benzene ring; more specifically it is a reaction in which the hydrogen atom of an aromatic ring is replaced as
22.7 ALKYLATION OF ESTER ENOLATE IONS
1084 CHAPTER THE CHEMITRY F ENLATE IN, ENL, AND a,b-unaturated CARBNYL CMPUND H H CA CL CoA + enol form of acetyl-coa _ C N NH acetyl-coa carboxylase H H R H carboxybiotin HN NH _ LC LCH LCLCoA + H H malonyl-coa
Course Syllabus Bioactive Compounds from Natural Origins
Course Syllabus Bioactive Compounds from Natural Origins Course title Bioactive Compounds from Natural Origins สารออกฤทธ ทางช วภาพจากธรรมชาต Code 162712 Credits 3(3-0) Prerequisite - Day/time/place Friday/9.00-12.00
Copyright 2010 Pearson Education, Inc. Chapter Fourteen 1
An alcohol has an OH bonded to an alkyl group; a phenol has an OH bonded directly to an aromatic ring; and an ether has an O bonded to two organic groups. Chapter Fourteen 1 Ethyl alcohol, dimethyl ether,
Chapter 2 Polar Covalent Bonds; Acids and Bases
John E. McMurry http://www.cengage.com/chemistry/mcmurry Chapter 2 Polar Covalent Bonds; Acids and Bases Javier E. Horta, M.D., Ph.D. University of Massachusetts Lowell Polar Covalent Bonds: Electronegativity
RESONANCE, USING CURVED ARROWS AND ACID-BASE REACTIONS
RESONANCE, USING CURVED ARROWS AND ACID-BASE REACTIONS A STUDENT SHOULD BE ABLE TO: 1. Properly use curved arrows to draw resonance structures: the tail and the head of every arrow must be drawn in exactly
Chapter 16 The Citric Acid Cycle
Chapter 16 The Citric Acid Cycle Multiple Choice Questions 1. Which of the following is not true of the reaction catalyzed by the pyruvate dehydrogenase complex? A) Biotin participates in the decarboxylation.
Chemical Bonds and Groups - Part 1
hemical Bonds and Groups - Part 1 ARB SKELETS arbon has a unique role in the cell because of its ability to form strong covalent bonds with other carbon atoms. Thus carbon atoms can join to form chains.
IDENTIFICATION OF ALCOHOLS
IDENTIFICATION OF ALCOHOLS Alcohols are organic compounds that which considered as derivatives of water. One of the hydrogen atoms of water molecule (H-O-H) has been replaced by an alkyl or substituted
21.9 REDUCTION OF CARBOXYLIC ACID DERIVATIVES
10 APTER 1 TE EMITRY F ARBXYLI AID DERIVATIVE TUDY GUIDE LIK 1.5 Esters and ucleophiles 1.17 Give the structure of the product in the reaction of each of the following esters with isotopically labeled
2. Couple the two protected amino acids.
General Considerations The Strategy of Peptide Synthesis Making peptide bonds between amino acids is not difficult. The challenge is connecting amino acids in the correct sequence. andom peptide bond formation
Electrophilic Aromatic Substitution Reactions
Electrophilic Aromatic Substitution Reactions, Course Notes Archive, 1 Electrophilic Aromatic Substitution Reactions An organic reaction in which an electrophile substitutes a hydrogen atom in an aromatic
SUMMARY OF ALKENE REACTIONS
SUMMARY F ALKENE REACTINS Alkenes are primarily prepared by elimination reactions of molecules that contain good leaving groups attached to sp 3 carbons. Examples of such reactions are dehydrohalogenations
1- Fatty acids are activated to acyl-coas and the acyl group is further transferred to carnitine because:
Section 10 Multiple Choice 1- Fatty acids are activated to acyl-coas and the acyl group is further transferred to carnitine because: A) acyl-carnitines readily cross the mitochondrial inner membrane, but
A disaccharide is formed when a dehydration reaction joins two monosaccharides. This covalent bond is called a glycosidic linkage.
CH 5 Structure & Function of Large Molecules: Macromolecules Molecules of Life All living things are made up of four classes of large biological molecules: carbohydrates, lipids, proteins, and nucleic
Addition Reactions of Carbon-Carbon Pi Bonds - Part 1
Addition eactions of arbon-arbon Pi Bonds - Part 1 3 δ+ 2 δ 3 3 3 + 2 3 2 3 What Is an Addition eaction? Addition reaction: Atoms or groups are added to opposite ends of a pi bond. X Y Why should I study
Determining the Structure of an Organic Compound
Determining the Structure of an Organic Compound The analysis of the outcome of a reaction requires that we know the full structure of the products as well as the reactants In the 19 th and early 20 th
Figure 3-1-1: Alkaline hydrolysis (saponification) of oil to make soaps.
Chapter 3 CHEMICAL MODIFICATION OF OILS AND FATS From the fats and oils obtained from natural resources, the majority of them are used directly or just after refinement. While the others are used after
1. The diagram below represents a biological process
1. The diagram below represents a biological process 5. The chart below indicates the elements contained in four different molecules and the number of atoms of each element in those molecules. Which set
CHEM 211 CHAPTER 16 - Homework
CHEM 211 CHAPTER 16 - Homework SHORT ANSWER Consider the Friedel-Crafts alkylation reaction below to answer the following question(s): 1. Refer to the reaction above. Draw the structure of the electrophilic
Lipids. There are 2 types of lipids; those that contain the structural component of a fatty acid; and
Lipids Lipids are biomolecules that contain fatty acids or a steroid nucleus. soluble in organic solvents, but not in water. named for the Greek word lipos, which means fat. extracted from cells using
Copyright 2000-2003 Mark Brandt, Ph.D. 54
Pyruvate Oxidation Overview of pyruvate metabolism Pyruvate can be produced in a variety of ways. It is an end product of glycolysis, and can be derived from lactate taken up from the environment (or,
2. Rank the following three compounds in decreasing order of basicity. O NHCCH 3 NH 2
1. To convert a nitrile to a primary amine you must: A) hydrolyze it with water. B) oxidize it with chromic acid. C) reduce it with hydrogen or lithium aluminum hydride. D) substitute it with an alkyl
carbon-carbon bond formation dehydration hydration decarboxylation oxidation reduction substrate level phosphorylation isomerization
1. A. Name each enzyme present in the citric acid cycle and specify which of the following describes the reaction that is catalyzed when the cycle functions in the physiological direction: carbon-carbon
Acids and Bases: Molecular Structure and Acidity
Acids and Bases: Molecular Structure and Acidity Review the Acids and Bases Vocabulary List as needed. Tutorial Contents A. Introduction B. Resonance C. Atomic Radius D. Electronegativity E. Inductive
What affects an enzyme s activity? General environmental factors, such as temperature and ph. Chemicals that specifically influence the enzyme.
CH s 8-9 Respiration & Metabolism Metabolism A catalyst is a chemical agent that speeds up a reaction without being consumed by the reaction. An enzyme is a catalytic protein. Hydrolysis of sucrose by
Lecture Overview. Hydrogen Bonds. Special Properties of Water Molecules. Universal Solvent. ph Scale Illustrated. special properties of water
Lecture Overview special properties of water > water as a solvent > ph molecules of the cell > properties of carbon > carbohydrates > lipids > proteins > nucleic acids Hydrogen Bonds polarity of water
Disaccharides consist of two monosaccharide monomers covalently linked by a glycosidic bond. They function in sugar transport.
1. The fundamental life processes of plants and animals depend on a variety of chemical reactions that occur in specialized areas of the organism s cells. As a basis for understanding this concept: 1.
Regulation of enzyme activity
1 Regulation of enzyme activity Regulation of enzyme activity is important to coordinate the different metabolic processes. It is also important for homeostasis i.e. to maintain the internal environment
ammonium salt (acidic)
Chem 360 Jasperse Ch. 19 otes. Amines 1 eactions of Amines 1. eaction as a proton base (Section 19-5 and 19-6) amine base -X (proton acid) a X ammonium salt (acidic) Mechanism: equired (protonation) everse
Writing a Correct Mechanism
Chapter 2 1) Balancing Equations Writing a Correct Mechanism 2) Using Arrows to show Electron Movement 3) Mechanisms in Acidic and Basic Media 4) Electron rich Species: Nucleophile or Base? 5) Trimolecular
Ch24_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
Ch24_PT MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question. 1) Substances originating in plant or animal material and soluble in non-polar organic solvents
IR Applied to Isomer Analysis
DiscovIR-LC TM Application Note 025 April 2008 Deposition and Detection System IR Applied to Isomer Analysis Infrared spectra provide valuable information about local configurations of atoms in molecules.
How To Understand The Chemistry Of An Enzyme
Chapt. 8 Enzymes as catalysts Ch. 8 Enzymes as catalysts Student Learning Outcomes: Explain general features of enzymes as catalysts: Substrate -> Product Describe nature of catalytic sites general mechanisms
The correct answer is d C. Answer c is incorrect. Reliance on the energy produced by others is a characteristic of heterotrophs.
1. An autotroph is an organism that a. extracts energy from organic sources b. converts energy from sunlight into chemical energy c. relies on the energy produced by other organisms as an energy source
CHAPTER 15: ANSWERS TO SELECTED PROBLEMS
CHAPTER 15: ANSWERS T SELECTED PRBLEMS SAMPLE PRBLEMS ( Try it yourself ) 15.1 ur bodies can carry out the second reaction, because it requires less energy than we get from breaking down a molecule of
for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency of the vibration
! = 1 2"c k (m + M) m M wavenumbers! =!/c = 1/" wavelength frequency! units: cm 1 for excitation to occur, there must be an exact match between the frequency of the applied radiation and the frequency
ALKENES AND ALKYNES REACTIONS
A STUDENT SHULD BE ABLE T: ALKENES AND ALKYNES REACTINS 1. Given the starting materials and reaction conditions, predict the products of the following reactions of alkenes and alkynes. Regioselective Markovnikov
Energy Production In A Cell (Chapter 25 Metabolism)
Energy Production In A Cell (Chapter 25 Metabolism) Large food molecules contain a lot of potential energy in the form of chemical bonds but it requires a lot of work to liberate the energy. Cells need