On Jargon

While reading Gary Stix's interview with Breaking Bad scientific advisor Prof. Donna Nelson, I stumbled upon a very telling chunk of text (emphasis mine):

"...the reduction step [for methamphetamine production] can vary from one synthesis to another, and there's a lot of differences in the reducing agents. And so I said, I don't know what reagent you want. They said to send them a list, and they liked the one that was aluminum-mercury because it would be easier for the actors to say those words.

That's another example of where I let [the producers] be boss. I wouldn't go back to them and suggest another reagent because it might be safer, cheaper, or have a higher yield. I just said, 'yes, sir.'"

"Sodium cyanoborohydride? No way am I saying that!"
Credit: AMC

Food for thought, especially for those of us trying to package chemistry in a more palatable format for folks outside the lab. But, the more I scratched my head over this situation, the more I wondered...are reducing agents that tough to pronounce?

Over at xkcd, Randall Munroe cheekily trounced our current cultural fixation on trochees, spoken words with a two-syllable stressed / unstressed pattern (ninja, pizza, Wal-Mart, Ke$ha, Xbox, etc.). "Aluminum-mercury," though taken right from the periodic table, hardly rolls off the tongue: seven* syllables!

"Classic" reagents for the reaction in question, like sodium cyanoborohydride (10 syllables) or sodium tris-acetoxyborohydride (12) certainly won't get by the writers without a grumble. But what about formic acid (4, with two trochees)? Raney nickel (4, two trochees) should also pass muster. Even better, maybe you could just fold the first two reductants into the generic "borane" (2, trochee) category?

Hey, AMC: Let's do lunch.

*And, of course, 8 if you live in the UK, and add that extra "i" to aluminium!

One More for the Road

OK, between my last post and that B.R.S.M. post, we've covered soda, wine, beer, carrots, salmon sperm, bone meal, coffee, and whiskey. If you include his comments, we can toss wool, almond meal, clay, and urine into the mix. But a recent J. Med. Chem. abstract may take the cake for me...

Poop.

Yup, here's the abstract, graphic and everything:

Source: J. Med. Chem. 2012, ASAP

What's the cecum, you ask? Great question! It's a "pocket" of large intestine, immediately following the small intestine and just before the colon. Apparently, it's renowned for two things: a high level of gut flora, and an anaerobic environment. When metabolism / fate scientists want to see what happens to an intestinal prodrug, this model comes into play.

Here's the prep, "fresh" from the Supporting Information:

"A solution of phosphate buffer (50 mM, pH 6.8) was prepared and deoxygenated by bubbling nitrogen for ten minutes. Male Sprague-Dawley rats were sacrificed and the cecum was exposed. The cecal contents were removed and used to make a 10% w/v suspension in the oxygen free buffer."

The microbe-rich slurry, after incubation with the compound at 37 degrees C with exclusion of oxygen, reduces down disulfide bonds, azo groups, even nitro aromatics to the parent anilines in "just a few hours."

Dunno about you, but I still think I prefer ol' Zn / AcOH. Probably smells a bit better, anyway.

Golden Bacteria?

An amazing breakthrough (!) recently made the rounds on Wired and Gizmodo: a synthetic chemistry / art-house installation in which microbes "...turn liquid gold into 24-karat gold." Two professors from Michigan State University - a microbiologist and a science artist - teamed up to produce the exhibit, entitled "The Great Work of the Metal Lover," which is currently on display at an Austrian art competition.

Credit: G.L. Kohuth | MSU

Hold your applause - the science doesn't travel well across multiple media outlets. The bacterium in question, Cupriavidus metallidurans, reduces gold(III) chloride solution (likely HAuCl4) and precipitates out pure metallic gold. C. metallidurans actually does have some 'super powers' - the last decade (PubMed) shows similar successes with copper, mercury, and lead. Heck, it's even been shot into space! 

But the MSU press release may win the hyperbole 'gold medal.' Here's a few choice lines:

"Cupriavidus metallidurans can grow on massive concentrations of gold chloride – or liquid gold, a toxic chemical compound found in nature"

Gold chloride, liquid gold? Oh, you mean the solid gold salt? With almost no tox data on the MSDS?  

"[the installation] uses a combination of biotechnology, art and alchemy to turn liquid gold into 24-karat gold"

Ye Gods. No alchemy here! I'm not a biochemist - just a #KnuckleDraggingOrganiker - but I'd guess there's a perfectly reasonable, well-studied reduction mechanism operating. Can I get a reductase over here? (P.S. the only "liquid gold" I know of is molten gold)

“This is neo-alchemy. Every part, every detail of the project is a cross between modern microbiology and alchemy"

No comment (see above). 

"...the researchers’ success in creating gold raises questions about greed, economy and environmental impact, focusing on the ethics related to science and the engineering of nature"

Unless we're talking phlogiston and aether here, there's no "creation" of gold: it's a reduction. And utilizing a bacterium to do what it likes to do anyway hardly sets up an ethical or social inquiry.

"[this work]...speaks directly to the scientific preoccupation while trying to shape and bend biology to our will within the postbiological age"  

I really don't understand what they're trying to say here. (Perhaps I need to read Art for Dummies...)

OK, scientific criticism aside, the work looks pretty neat. How often do you get to see electrochemistry in an art exhibit? In the end, I guess the ends justify the means - if just a few people look at it, and think "I wonder how that works?" it will have served its purpose.