Molecules Study Guide - DRAFT


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Molecules Study Guide - DRAFT

  1. 1. Molecules Study Guide - DRAFT Chapter or Molecule Chemical Structure Biochemical relevance Physical property relevance subject Alkanes Methane CH4 Marsh gas, produced by methanogenic Mp. = , Bp = , gas at STP. Because of the very bacteria low temperature on Saturn’s moon Titan, methane forms clouds, rain and lakes, eroding rocks made of water ice! Also found in deep ocean deposits combined with water ice – the ice that burns! Alkanes Butane CH3CH2CH2CH3 Liquid in lighters, gas at atm. pressure. Fits into the hydrophobic space in the helical starch structure. Alkenes Ethylene Gas that causes fruit ripening and is responsible for “one bad apple spoils the bunch” and the effectiveness of fruit ripening containers. Preserve fruit in refrigerator by destroying ethylene (use KMnO4) Alcohols, Capsaicin Pain medication Solubility, washing off tongue Phenols, Lipids Phenols, Urushiol Washing off skin Acids & Bases Alkenes, Brominated lipids vegetable oil Lipids Trans fat Implicated in heart disease Higher melting point than cis Lipids Taurine Found in bull bile. A building block of Very soluble due to zwitterion (positive and bile acids. Found in some energy negative charge in a neutral molecule)
  2. 2. drinks, but problems when mixed with alcohol. Banned in France and Japan. Disulfides/ Hair proteins permanent chemicals, hair Thiols Skunk thiols Defense, oxidize with bleach or peroxide Lewis N2O anesthetic, laughing gas Soluble in fat, so it is used as whipped cream Structures propellant. When expelled, it creates the foam and whips the cream. Lewis N2O4 Space shuttle fuel. When mixed with Structures CH3NHNH2, it reacts to produce energy, no catalyst or spark required (called a hypergolic fuel.) This property is necessary for rocket engines that must operate outside the atmosphere, in the absence of oxygen. Carbohydra Propofol vs Drug metabolism Acidity tes/ phenols aromatic version Alkenes Beta- Vision Conjugation carotene Alkenes Lycopene Prostate health Conjugation Alkenes, Menthol, Terpenes. Enantiomers of carvone have Chirality carvone, different flavors (mint vs. rye) other spices Chirality Omeprazole, Drug enantiomers often have different S- biological properties, “chiral switch” omeprazole strategy Aromatics, Benzene Carcinogen Aromatic stacking as a type of London force
  3. 3. DNA Alcohols, Ethanol Alcohol dehydrogenase, some asians Oxygenator in gasoline enzymes lack enzyme, blood alcohol test Aromatics Sulfa drugs Pre-penicillin antibiotic Water solubility Alkenes Bilirubin Jaundice and its treatment Conjugation Alkenes Chlorophyll, Grass, blood pigments Conjugation heme, vitamin B12 Ethers MTBE Solubility in water Chirality Thalidomide Enantiomer biochemical properties Alcohols, Isopropanol Denaturation by 70% but not 90% Proteins Aromatics Thyroid hormone Alkenes Corn borer Cis/trans isomers pheromone (connection 3B Alkenes, Retinal Cis/trans isomer conversion in vision. Conjugation Aldehydes Retinol analog research by nakanishi. Reaction of coupling aldehyde to protein Alkenes Polymers Aromatics Benzo[a]ant Carcinogen hracene Aromatics Food dyes Conjugation (4E) Ethers Diethyl Anesthetic Flammable ether (5D) Protein, Egg white Anti mercury poisioning treatment
  4. 4. thiols Chirality Ibuprofen ChemConne ctions 9A – muscone, ionone, citronellal Aldehydes Vanillin Nice smell Artificial vanilla vs other artificial flavors Soap Acid Penicillin NH β-Lactam antibiotic. The ring strain S derivatives O CH3 energy in the β-lactam ring is released N CH3 O when the drug reacts with an enzyme HO O that constructs the outer membrane of the bacteria. Drug resistant strains have developed a b-lacamase enzyme. Carbohydra Xylulose tes Hyaluronic acid Heparin Amylose, amylopectin , glycogen Carbohydra Corn syrup Made by hydrolysis of sucrose tes followed by invertase Lipids Arachidonic Cyclooxygenase converts it to acid leukotrienes Leukotriene s, prostaglandi
  5. 5. ns Steroid ring Hans Selye’s house, stress steroid parent research Acid Acetylcholin H3C + O CH3 Important neurotransmitter, which is Quaternary ammonium is always positively N derivatives e H3C hydrolyzed by the enzyme charged so the molecule is very soluble in CH3 O acetylcholine esterase to “turn off the water. message” and prepare the nerve for another signal. Inhibitors of this enzyme are important drugs and poisons. Acid Barbituates derivatives Alkanes Tetracycline Named after the fact that it has four or three , tricyclic rings antidepressa nts Chemical Methyl Produced in urine by catabolism of ? in structures, thioacrylate asparagus, responsible for smell after Metabolism digesting asparagus Chemical Diallyl Produced by onions and allium sp. And structures disulfide generates sulfuric acid in eyes? Causing lacrymation Proteins, SAHA This drug inhibits the activity of lysine DNA deacetylase., anticancer agent DNA, Nucleosome Lysine residues that are acetylated are Proteins, core particle no longer protonated at physiological Acid pH, so they are neutral rather than + derives. charged. These groups therefore have less attraction for the negatively charged phosphate groups on DNA,
  6. 6. and the DNA can unwind. Aspartic acid and Glutamic acid residues can be esterified to eliminate negative charges… Carbohydra Starch In helical form, interior of helix is hydrophobic, tes allowing I2 or even butane to be absorbed by starch. Enzymes Carbonic One of the most prevalent enzymes in anhydrase blood, this enzyme is responsible for catalyzing the conversion of carbonic acid to carbon dioxide, rapidly equilibrating the CO2 concentration in lungs and muscle tissues so rapid exchange of CO2 can occur. Drug Warfarin Anticoagulant derived from coumarin, design which was discovered in moldy sweet clover to cause internal hemmoraging in cattle. Enzymes Furanocoum In grapefruit juice, it is an inhibitor of arins cychrome p450(?) Vanillin Carvone Laetrile Cinnamalde hyde/Cinna mic acid Lipids Solanin Cholesterol Digitalis Acids Ammonium
  7. 7. thioglycolat e Palmolive detergent Xylitol Heparin NAG-NAM Lysozyme Oxalic acid Molecule Chemical Structure Biochemical relevance Physical property relevance Acetylcholine CH3 O Acetylcholine is an important neurotransmitter. The Quaternary ammonium ion is always + charged, which H3C + signal is turned off when the ester bond is hydrolysed. means this molecule is very soluble in water regardless of N pH. A counter ion must be present as well, but is not shown H3C O CH3 in the structure at left. Lactomer ® stitches Nylon . Kevlar Protein Barbituates H O N O R1 NH R2 O Acetic acid
  8. 8. Acetyl O OH salicylic acid (aspirin) O CH3 O Aspartame ® This sugar substitute is composed of two amino acids, O phenylalalanine and aspartic acid, linked by an amide bond, and a methyl ester of the phenylalanine. Hydrolysis O OH of the ester occurs in water with heat, producing H3C NH methanol. Consequently, aspartame should not be used in O NH2 foods that will be heated, e.g. cake batter. Complete hydrolysis occurs in the stomach, giving methanol, O phenylalanine, and aspartic acid. Children and young adults with the genetic disorder phenylketonuria (PKU) must scrupulously avoid phenylalanine in their diets, and must therefore avoid this artificial sweetener. Penicillin NH β-Lactam antibiotic. The ring strain energy in the β- S CH3 lactam ring is released when the drug reacts with an O N CH3 enzyme that constructs the outer membrane of the O bacteria. Drug resistant strains have developed a β- O HO lacamase enzyme. Clavulanic This β-Lactam does not have antibiotic activity, but it is acid an inhibitor of the β-lactamase enzyme that gives some OH O bacteria resistance to this class of antibiotics. The N potassium salt clavulanic acid is combined with a β- O O lactam antibiotic to reduce the development of resistant HO bacteria. One example of this drug combination is Augmentin, a combination of amoxicillin and potassium clavulanate. Fatty acids Fatty acids store energy and are building blocks for Form micelles in water because the COOH end is soluble in lipids. Enzymes create fatty acids from two-carbon water but the alkane chain is not. The Ca2+ and Mg2+ salts of building blocks, so even numbered chains are much more fatty acids are insoluble in water and form soap scum when common in nature than odd numbered chains. soap is used in hard water, which contains these ions. Cis Unsaturations are almost always cis, which introduces double bonds reduce the melting point of fatty acids
  9. 9. kinks into the chain. because the kinks interrupt stacking interactions. Acetyl-CoA Molecule Chemical Structure Biochemical relevance Physical property relevance Quinine Known for over 300 years as a treatment (but not a cure) Amines have a bitter taste. Amines (and alkaloids) are more CH2 H for malaria, discovery of this alkaloid from the bark of soluble as the positively charged cation. Quinine is HO N the Cinchona tree had the impact on medicine that commercially available as the salt with sulfuric acid, called H3CO gunpowder had on warfare. Found in non-medicinal the sulfate. Amines also readily oxidize in air, but the quantities in tonic water. protonated form is much more stable to oxidation. Tonic N water fluoresces because of aromatic rings in quinine. Lidocaine CH3 Common local anesthetic (e.g. injection before stitches). The HCl salt of lidocaine is more soluble in water and less NH susceptible to oxidation than the free amine, and this is the N CH3 form used for injections. O CH3 CH3 Cocaine CH3 O Alkaloid found in coca plants. Flavoring in Coca-Cola The naturally occurring protonated form is not very volatile N CH3 includes extract of same plant, after cocaine has been (it has a high boiling point), making it difficult to ingest by O removed. The process is carefully monitored by the FDA. smoking. However, the neutral amine is more volatile. “Crack” cocaine is the neutral (or “free base”) form of the O amine, which is more volatile and can be smoked. O Caffeine O CH3 Alkaloid found in coffee and tea. Protonated form is more water soluble and less volatile than neutral, unprotonated form. H3C N N O N N CH3
  10. 10. Nicotine N Addictive component in cigarettes, where it is normally The naturally occurring protonated form is less volatile than CH3 found in the hydrochloride form. the neutral form. Adding ammonia (a base) to tobacco leaves releases more into the gas phase – chemical trick of N cigarette manufacturers to increase the dosage of nicotine and the addictive power of a cigarette. Quaternium-1 Preservative used in cosmetics (look for it on your Example of a quaternary amine which is positively charged 5 shampoo bottle), it releases formaldehyde. at any pH. Morphine, CH3 Opium poppy contains morphine (R1=R2=H) and codeine Heroin (R1=R2=COCH3) is a non-naturally occurring codeine, N (R1=CH3, R2=H) , and poppy seeds contain trace derivative of morphine, and example of a chemical heroin H amounts. Eating 2-3 poppy seed bagels can result in a modification of a natural substance to produce a drug with positive drug test for opiates. For this reason, poppy different bioactivity. seeds are banned in Singapore and not served on US military bases. R1 O O O R2 O Ergotamines, Ergotamines are produced by the ergot fungus which A chemist created a derivative of an ergotamine, Lysergic H3C LSD N grows on rye. These alkaloids cause ergotism, a type of Acid Diethylamide (LSD) which is a powerful psychotropic H3C H NH poisoning. Entire towns have been poisoned when the drug. N baker’s flour was contaminated. Rye must be carefully H3C monitored to prevent formation of the ergot fungus. LSD
  11. 11. O PABA & Para aminobenzoic acid (PABA) or Octyl N,N-dimethyl The aromatic part of the molecule absorbs UV light (due to octyl N,N- O - PABA are common active ingredients in sunscreen. conjugation) and protects skin from sunburn. PABA is dimethyl water soluble because it is in the zwitterions form, but octyl PABA H3N + dimethyl PABA is much less soluble in water and therefore PABA (zwitterion) can be used in a sunscreen that does not wash off as easily. O (A zwitterion is a neutral molecule which has a + and – O 7 CH3 charge.) H3C N CH3 Octyl dimethyl PABA Putrescine NH2 Responsible for the stench of dead animals, along with Amines can be very foul smelling compounds! H2N cadaverine and many other chemicals. Spermine At physiological pH, this molecule is protonated at each NH NH2 nitrogen, making it a polycation. This is strongly attracted H2N NH to the negatively charged phosphates in DNA. Spermine is an important DNA stabilizer. Carbon CO2 equilibrium is responsible for an important pH buffer dioxide, in blood. The enzyme carbonic anhydrase catalyses the carbonic acid, H2O equilibrium. Excess CO2 in blood can result in excess bicarbonate, carbonic acid and lead to low blood pH (respiratory and carbonic acidosis). Hyperventilation can lower the amount of CO2 CO2(g) CO2(soln.) H2CO3 H+ + HCO3- anhydrase and lower amount of carbonic acid in blood (respiratory alkalosis, “sprinters trick”) H2O Pressure equilibrium in a soda bottle demonstrates the first carbonic anhydrase reaction shown; the low pH of soda and increase in pH as CO2 is lost demonstrates second reaction shown. Albuterol See Chemical Connections