Differences between my American and Danish laboratories

The synthetic laboratory I worked in at UC Davis focused on heterocyclic aromatic methodology.  I spent five years figuring out what happens to bis-(o-NO2-phenyl)isoxazoles when you heat the crap out of them in the presence of ketones (like acetone…nail polish remover), iron, and acetic acid.  Turns out it makes interesting glowy shit that changes colors based on it’s environment.

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That’s pretty cool.

This type of chemistry has it’s limitations just like any other, but it sure was fun to take pictures of.  Interestingly, the three vials above contain the same exact compound in different solvents (green= ethanol, orange = acetic acid, blue = ethyl acetate).  Spiffy.  Compounds like this have potential use as tracker molecules.  If you can tag them onto a drug and follow it’s path through the body, based on the color of the observed fluorescence you can glean important information about the environment the drug is in in the body in a non-invasive manner.  They could also potentially be used as chemical sensors.

A key thing that my work lacked as a graduate student was the ability to control the stereochemistry of the reactions I developed.  I can hear you asking “why do I care?”  Do you remember in the 1950’s and 60’s when doctors were prescribing thalidomide as a morning sickness drug for pregnant women? Remember how it caused massive birth defects and was later recalled?   Turns out that one enantiomer (non-superimposable mirror image…think of your right hand vs your left hand) was effective as a morning sickness drug and the other enantiomer (the other hand in our analogy) caused terrible birth defects in the developing child.  So the answer to why do we care about stereochemistry is simple: we can alter the effect of a substance pretty fucking dramatically simply by changing its’ stereochemistry.  As the pharmaceutical industry advances, it will become more and more important to be able to control the stereochemistry of every step of a chemical process.  Thus the need for chemical research addressing the issue.  The lab I am working in at Aarhus University in Denmark focuses on exactly that.

As PhD chemists, we have an ‘academic lineage’ that we can trace.  People often times refer to it as your pedigree (so happy I get the same terminology as a dog).  The person my advisor worked for as a graduate student is my academic grandfather/grandmother and so on.  Both Robert Burns Woodward and Roald Hoffman appear in my academic lineage.  These guys developed some of the most important and fundamental organic chemistry involving the formation of all carbon based cycles.  Woodward received the nobel prize in 1965 for “his outstanding achievements in the art of organic synthesis” and Hoffman (with Kenichi Fukui) received it in 1981 for “for their theories, developed independently, concerning the course of chemical reactions.”  These guys are chemical badasses.  Why do I mention this?  The project I am working on is a direct product of the chemistry they developed.

My new project involves the stereocontrol of ‘higher order cycloadditions.’  It means testing some of the predictions they made in the 60’s and 70’s that were un-testable at the time because we hadn’t developed the chemistry yet.  It involves combing two, 4 to 8 atom pieces in a stereoselective fashion (in such a way to only make the right handed version or the left handed version…just not both) to make a large cycle.  It’s all new ground that I have never walked on before, and I am intimidated and excited.  I am learning a ton.  There is also a certain cyclic beauty (pun intended) to working on this chemistry.  It feels like stepping in the shoes of my great great great great chemical grandfathers.

In a much less heady and more practical sense my Danish labs are incredibly well stocked.  While my American labs had all the tools necessary to organic synthesis, these Danish labs have all the newest and best equipment.  Some of the safety rules are a bit more lax, and some are far more strict.  In the US there was no way in hell I could wear stockings in lab and have them pass as pants.  Here?  Not a problem.  I can wear shorts if I want.  It feels odd and is not likely something I will do.  The safety rules I am used to exist for a very good reason (for example, see: UCLA incident).  On the other hand, in my American labs liquid waste containing halogens and liquid waste sans halogens were simply combined for disposal.  Here, there are strict rules about separating them (primarily for cost reasons due to differences in disposal as far as I understand).

If you’ve made it this far, I think you deserve a reward.  To this end here are some pictures of Denmark:

 

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Moonrise over the bay from my  balcony.

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Aarhus from above (take from the roof of the Aros art museum).

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Book nook in Copenhagen.

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Restaurant in Copenhagen…not sure what kind of Thai food they serve but I would love to find out.

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Beautiful botanical gardens in Copenhagen.

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If I didn’t already have a pikachu, I would have bought some pizza.

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Magic duck!

-Crash

 

 

 

 

 

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