Penicillin: Wonder Drug

Penicillin has become synonymous with modern medicine, but this wonder drug has only been around for roughly 70 years. Before penicillin the mode for treating infection was not nearly as effective. When it was first debuted, before WWII, it was the biggest thing to hit the medical community and became the number one choice for treating a wide range of infections. Some of the most popular prescriptions belonged to people suffering from Syphillis, Strep, or Staph, as well as other. The problem with Penicillin being so effective against all of the aforementioned "bad actors" is that it was used too much, and have lead to antibiotic resistance in several bacteria species.
  Penicillin contains three chiral centers and S,R,S steriochemistry. Look to the diagram for exact locations.

http://www.medicalnewstoday.com/articles/216798.php

http://itech.dickinson.edu/chemistry/?cat=65

CHIRAL MOLECULES---PENICILLIN

Today, the use of penicillin and other antibiotics are common place. The various antibiotics are used to treat a number of what are now common diseases and to prevent the onset of infections when our skin, our first barrier to fight off disease, is somehow broken through a simple cut or a more serious wound. However, many diseases and simple wounds that are so easily treated today because of the availability of antibiotics has not always been available. Antibiotics are a relatively recent discovery and the first practical one, penicillin, was not available until the early 1940s. Penicillin’s are natural product that  were the first antibiotics used in clinical practice. They are based on the original penicillin- G structure and inhibit bacterial cell wall synthesis; and are generally bactericidal. These products are effective against gram positive bacteria such as staphylococci, streptococci, syphilis, and gram negative bacteria such as meningococci, Treponema, Borrelia and Leptospira. The most common side effect of penicillin is diarrhea. Also, nausea , vomiting , and upset stomach can been seen as well. Moreover, the stereochemistry on penicillin indicate how diverse the compound is and it reveals its importance. 

The carbon numbered 2 is S, carbon 5 is R and carbon 6 is S 

Reference:

http://www.botany.hawaii.edu/faculty/wong/BOT135/Lect21b.htm

CHIRAL MOLECULES-PENICILLIN AND ITS EFFECT

There are different types of penicillin and used to treat different kinds of infections, such as skin infections, dental infections, ear infections, respiratory tract infections, urinary tract infections, gonorrhea, and other infections caused by bacteria. These drugs isnot effective  for colds, flu, and other infections caused by viruses. Examples of penicillins are penicillin V (Beepen-VK, Pen-Vee K, V-cillin K, Veetids) and amoxicillin (Amoxil, Polymox, Trimox, Wymox). Penicillins may be mix with other ingredients called beta-lactamase inhibitors, which protect the penicillin from bacterial enzymes that may destroy it before its function. Thus, penicillins are obtained via prescription.

The original form of penicillin is called penicillin G. It is a narrow-spectrum antibiotic, which can be destroyed by stomach acid, but it is still useful against anaerobic bacteria. Newer penicillins are resistant to stomach acid, such as penicillin V, or have a broader spectrum, such as ampicillin and amoxicillin.

Penicillins are effective against infections in many parts of the body, including the mouth and throat, skin and soft tissue, tonsils, heart, lungs, and ears. However, since many bacteria are resistant to penicillin, it is often wise to do a culture and sensitivity test before using penicillin. In some cases, there are only a few types of bacteria that are likely to be a problem, and so it is appropriate to use penicillin without testing. For instance, dentists often prescribe penicillin to prevent infections after dental surgery.

Penicillins are usually very safe and the greatest risk is an allergic reaction, which can be severe. People who have been allergic to cephalosporins are likely to be allergic to penicillins. Moreover, people with certain medical conditions or who are taking certain other medicines can have problems if they take penicillin. 

In conclusion, penicillin is a compound with three chiral center and the stereochemistry is as follows:

The carbon labeled 2 is S, carbon labeled 5 is R and carbon labeled 6 is S.

 

 

http://www.healthofchildren.com/P/Penicillins.html#ixzz2jKq9AAVS

Aspartame

        The goal of many health conscience individuals these days has been to decrease calorie and sugar intake. Back in the 1980’s an artificial sweetener by the name of Aspartame hit the markets. This compound comprised of aspartic acid and phenylalanine seemed to combat higher caloric intake and also proved to be a healthy alternative to sugar. Aspartame is approximately two hundred times sweeter than regular sugar thus it takes much less of it to achieve the same sweetness factor.  Whoaaa! Beneficial right? For this reason yes aspartame is very beneficial but what people cease to understand is that aspartame actually causes more harm than good.

         One way in which Aspartame proves to be detrimental is the fact it actually increases your craving for carbohydrates. So while you are decreasing calories you are simultaneously increasing your carbohydrate intake. How can one lose weight by decreasing calories but still increase the number of complex sugars (carbohydrates)? Does not make sense at all.

Now this previous reason may not be enough to convert your grand parents and the rest of the artificial sweetener fans to go back to ordinary sugar but it gets worst. I believe every one knows what formaldehyde is used for. It’s a major contributor in what is known as embalming fluid. One of the main components of this great artificial sweetener Aspartame is wood alcohol. You might ask, what does wood alcohol have to do with anything? Well at temperatures exceeding 86 degrees Fahrenheit the wood alcohol in your precious artificial sweetener can be converted to formaldehyde. The average humans body temperature is what?.... I believe it’s a bit higher than 86 degrees. Whooooa. Not only is it gross to think that we may have formaldehyde in our systems but it is actually toxic. Two poisons that you may have heard of are cyanide and arsenic and formaldehyde is grouped in the same class of poisons. What makes formaldehyde different from these other two poisons is its incubation period. It takes much longer for one to feel the affects of formaldehyde and thus I’d like to name it the “Silent Killer”. There are over 90 some odd symptoms of aspartame poisoning all of

which arise from neurological problems.

         Ok so does this prove anything to you artificial sweetener lovers? I know one thing, id much rather gain a few pounds from regular sugar than to have the neurological symptoms stemming from the diet coke I’ve been drinking for the past 10 years. Take it for what its worth!!!

http://www.cancer.org/cancer/cancercauses/othercarcinogens/athome/aspartame

Valine: Body Builder’s Drug?

Valine: Body Builder’s Drug?

Valine is an amino acid that is obtained by hydrolysis of proteins and is an essential amino acid.  Valine is a chiral molecule naturally found in dairy, meat, grain, mushrooms, soy and peanuts. Foods with the highest amount of valine include egg whites(3371mg), elk (3200 mg), sea weed (2785 mg), soy protein (2425 mg), turkey (2380 mg), cod (2251 mg), lamb (2214 mg), cottage cheese (2131 mg) and white mushrooms (2110 mg).

It has a stimulating effect and is needed for muscle metabolism, repair and growth of tissue and maintaining the nitrogen balance in the body and can be used as an energy source. Valine is found in high concentrations in the muscle tissue. There are indications that valine may be beneficial in treating or reversing hepatic encephalopathy (disorder of the brain) or alcohol related brain damage along with degenerative neurological conditions. It may also be helpful n treating liver and gallbladder disease. If deficient in valine may effect myelin covering the nerves and may lead to MSUD, a disorder in which the body is unable to process certain amino acids.

Bodybuilders use valine to promote muscle growth, tissue repair and energize, although there is little scientific backing of these claims. There are however studies that show that alanine, leonine and isoleucine are useful in restoring muscle mass in people that suffer from liver disease, injuries or have undergone surgery.

Works Cited:

"Foods Highest in Valine." Self Nutrition Data. Self, n.d. Web. 31 Oct. 2013. <http://www.anyvitamins.com/valine-info.htm>.

"Valine Amino Acid Information Page." Foods Highest in Valine. Sallamander Concepts (Pty) Ltd., 5 Sept. 2013. Web. 31 Oct. 2013. <http://nutritiondata.self.com/foods-000088000000000000000.html>.

Chiral Molecule: Life with Amino Acid Isoleucine

Amino acids are the primitive compound that have been theorized to have roots dated back to 4.7 billion years ago when the Earth was born. During this time, Earth does not have an atmosphere to support life. However, studies and experiments such as the Miller-Urey experiment, have replicated an early Earth-like environment and found that amino acids formed. Amino acids are the builders of proteins. There are 20 different kinds of amino acids that built thousands of different proteins similar to 26 alphabet letters that make up thousands of English vocabulary.

Within the structure of Isoleucine, it has 2 chiral centers at adjacent carbons. Isoleucine is one of the most essential amino acids that promote muscle recovery after physical exercise and regulates hemoglobin in blood sugar and energy levels. The first Isoleucine is D, which occurs rarely in nature and there is L that can be found abundantly in nature. Both are mirror images of each other, but the amines and methyl group changed position making them enantiomers. Both are favorable in athletics and can be taken as a medication to regulate blood sugar and energy efficiency.

References:
http://www.rsc.org/chemistryworld/2013/06/switching-chirality-amino-acids-nickel-catalysis

http://www.biology.arizona.edu/biochemistry/problem_sets/aa/Isoleusine.html

http://guweb2.gonzaga.edu/faculty/cronk/biochem/I-index.cfm?definition=isoleucine

Drink, Drank, Drunk!

Most people who are reading this are familiar with wine, and for good reason --> like, when studying for Organic Chemistry tests/other challenging subjects!  As you may or may not know, alcohol is one of the oldest forms of currency and has therefore been studied quite extensively.  It should also come as no surprise that Tartaric Acid (found in grapes, bananas, and tamarinds), was how the discovery of chirality came to pass.
In ~800AD; the alchemist, Hayyan, was able to produce a rough product called 'tartar'.  'Tartar', is still used today in many industries like, beer, food, medicine, etc.  It was in 1832, that Jean Baptiste Biot observed that light rotates when polarized light was exposed to it.  This observation lead to Louis Pasteur taking it one step further and examining the phenomenon under the microscope, thereby helping us to not just observe chirality for the first time, but also to find new ways to apply this new found knowledge.  
The concept of chirality is extremely important when looking at one of today's biggest industries, drugs.  Many of the drugs that have been studied/developed/perfected over time have been developed as chiral compounds because the receptors in the human body are chiral, example being the psychiatric drugs.  It is now my hope that the next time you open a bottle of wine, that you will think about all the advancements that we have made as a result of studying alcohol - just don't study too hard or you may have to worship the porcelain god.  
 

(I tried to draw this in the paint program for better steriochemistry, but I wasn't able to paste it... soooo Wikipedia's pictures will have to suffice)



http://en.wikipedia.org/wiki/Tartaric_acid
http://xudaphne01.wordpress.com/2013/07/23/the-uses-of-potassium-tartrate/
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC161712/