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A Broad Scientific Question: What is the nature of matter? Organic Chemistry: The study of carbon containing compounds. Since virtually all naturally occurring compounds contain carbon, organic chemistry is inextricably tied to living systems.
O O H 3C Plant Extraction H 3C O H 3C O H 3C Purple Foxglove, i.e. Digi tal is P urpur ea HO OH O O OH O OH O H 3C H H Steroidal Aglycon The "War-Head" of Digitoxin H OH Digitoxin - A Drug Based on Digitalis Extract Used to Treat Congestive Heart Failure and Atrial Fibrillation H
N N O Popcorn Aroma Me
N N
OMe Me
N N
OMe Me Me
OH OMe
OH OMe
O OMe NH2
O H Vanilla Aroma
Clove Aroma
Grape Aroma
O H3C O Pear Aroma O H3C O(CH2)7CH3 Orange Aroma H3C CH3 H3C O
O CH3 H3C O
O CH3
O C H
Left Hand Right Hand (+)-Carvone (Caraway)
O C H
(-)-Carvone (Spearmint)
Tetrahedral Carbon Centers Possessing Four Different Groups Can Exist as NonSuperimposable Mirror Images They are Enantiomers.
O N O H C O N H O O
O N C H O N H O H 3C H 3C
NH2 O
H 2N O
SH OH
HO HS
CH3 CH3
If a molecule has n-chiral centers, there are 2n possible combinations possible, termed stereoisomers. The FDA now requires that chiral molecules be prepared as single entities. Over 50% of the worlds top-selling drugs are single enantiomers and it is estimated that 80% of all drugs currently entering development are chiral and will be marketed as single-enantiomer entities.
H 3C O NH O O OH OH O O H O O O CH3 O O O OH
Taxol - Bark of Pacific Yew Tree Potent Anti-Cancer Agent 11 Stereocenters 2048 Possible Isomers!
O O CH3 H H
OH
CH3 CH3
O O H3C
Plant Extraction
H OH
O HO OH
OH
O OH NH2
2
O CO2H
HO O NMe HO Morphine
O OH O O CH3
Acetosalicylic Acid
One important side effect is nausea and vomiting, which plays an important role in the historical significance of physostigmine and calabar bean. In the past, calabar bean was used in trial by ordeal by the Efik Uburutu people in Nigeria to determine if a suspected person was guilty of a crime. After ingesting an herbal drink containing ground calabar bean, if the suspect vomited, they were declared innocent. If they didnt vomit, the suspect was declared guilty, and would die soon after. Medicinal applications of physostigmine-containing calabar bean were first studied in 1864, and further development has resulted in a powerful therapeutic agent.
Naproxen (Aleve etc.): Phenylpropionic acid derivative that is commonly used for the treatment of moderate to severe pain and inflammation associated with arthritis. It was first marketed as a prescription drug (Naprosyn) in 1976 and became available over-thecounter as naproxen sodium (Aleve) in 1994.
Ketoprofen (Orudis, Oruvail, etc.): Phenylpropionic acid derivative that is commonly used for treatment of inflammatory pain associated with arthritis. It is a racemate with only the (S)-enantiomer possessing pharmacological activities. It is also a common analgesic and is used fever-reducing in horses and some small animals.
Diclofenac (Voltaren, Olfen, etc.): Phenylacetic acid derivative that is commonly used for the treatment of inflammation and joint pain caused by rheumatoid arthritis, osteoarthritis, ankylosing spondylitis etc. It was developed by Ciba Geigy (now Novartis) in 1973 and was first introduced into the UK in 1979.
Ketorolac (Toradol, Acular): Heterocyclic acetic acid derivative that was approved by FDA in 1989. Recent studies showed that it is effective for reducing post-operative pain. This drug is not available over-the-counter in the United States and a prescription is required for administration.
HO
NH3Cl OH H 2N
NH2 N N SO2NH2
Prof. M. J. Krische
Despite its wonders, penicillin is not effective against tuberculosis a bacterial infection of the lung. During the 19th century, up to 25 per cent of deaths in Europe were caused by this disease (although 90% of infections are asymptomatic). Over the past two centuries, TB has claimed over 2 billion lives. A third of the world's population are thought to be infected with M. tuberculosis, and new infections occur at a rate of about one per second. Streptomycin is antibiotic produced by soil bacteria originally isolated by Waksman and Schatz in 1947. It is a mainstay of tuberculosis therapy. Because streptomycin-resistance arises during treatment, the antibiotic is usually used in combination with other drugs, such as isoniazid or rifampicin, another natural product from soil bacteria isolated in 1957. Despite all the drugs available today, TB is still a problem in developing nations. The highest incidences (up to 80%) are in countries in Africa, Asia, and Latin America only 5 10% of the US population tests positive for TB. The World Health Organization estimates that each year 3 million people die from TB. Today, there are strains of TB resistant to any known antibiotic. In New York City, 19% of TB is resistant to the two most powerful drugs. It is now feared that the disease will spread to other areas in the U.S. before there is a cure.
Me O Me HO HO Me HO O Me O
NMe2 HO Me O Me O O Me Me O Me Me OH OMe Me Me
OH OH O
OH OH O OH Me N Me HO HO Me HO O Me O
Me HO Me O Me O O Me Me
NMe 2
Me Me
OH OH O
OH OH O OH
OH OMe
Erythromycin A
Azithromycin
Me Me Me Me Me Me 7 polypriopionate units
Prof. M. J. Krische
The Cinchona tree was originates from the slopes of the Andes. Its ability to cure malaria was discovered by Jesuit monks and the anti-malarial value of Cinchona became more widely recognized. So valuable was the bark that at one time, bark powder was often matched by its weight in gold. Indeed, over-harvesting of the bark nearly decimated the population of the tree in its native habitat. Fortunately, Dutch adventurers smuggled a few seedlings out of Peru in the 1860s, and used them to set up large plantations in Java. In WWII, the Japanese military conquest cut off access to quinine from Java, which accounted for 95% of the world supply. This led to the death of over 60,000 US troops died in WWII due to malaria infection.
Currently, an estimated 200 million to 300 million malaria infections occur each year, with 2 million to 3 million deaths one death every 12 seconds. 90% of all cases occur in Africa. 5% of African children (3,000 each day) die of malaria. The World Health Organization (WHO) ranks malaria first among human parasitic diseases in terms of socio-economic and public health importance. Due to global warming and drug-resistantance, malaria is undergoing a dramatic resurgence. Since recorded history until today, more human deaths are attributed to malaria than any other cause.
Cyclamate: Discovered in 1937 at the University of Illinois by graduate student Michael Sveda, the FDA banned its sale in the United States in 1969 because intestinal bacteria could desulfonate cyclamate to produce cyclohexylamine, a compound suspected to have some chronic toxicity.
Aspartame: Discovered in 1965 by James M. Schlatter, it is 180 times sweeter than sucrose. This sweetener is marketed under a number of trademark names, including Equal, NutraSweet, and Canderel. It is used in approximately 6,000 consumer foods and beverages.
Sucralose: Discovered in 1976 by Leslie Hough, sucralose was first approved for use in in 1998. It is 600 times as sweet as sucrose and can be found in more than 4,500 food and beverage products. It is used because it is a no-calorie sweetener and is safe for consumption by diabetics. It is marketed as Splenda.
4 Linear Steps, H2O is Only Stoichiometric Byproduct Catalytic Chemistry versus Stoichiometric Reagent Abundant Starting Materials - Minimal Preactivation