Meanwhile, Elsewhere...

I've been seeing other blogs behind my blog's back. Please don't tell anyone!

First up, do you like art? Like Chemistry? Hop on over to Nat. Chem's Blogroll ($).

Second, I talk about LeBron James promoting soluble polymer breath strips at Chemistry Blog.

Thirdly, check out the latest on the BMS-Inhibitex HCV drug, over at The Haystack.

Note: Back in 1949, we didn't have names or properties for anything beyond element 96!
(We've since added almost 20 more.)
Source: Life Magazine | Lots of Chemists on Twitter

WWWTP? Time's Aspirin Structure Causes Headache

While reading through the 2012 "Time 100" issue, I happened across a flow chart with a certain chemical structure. The chart, dubbed "Influence: A Brief History" (also a couched ad for Citibank) details epochal moments in human innovation, from Frankenstein to Dolly the cloned sheep.

Next time, how about using SciFinder? Or an encyclopedia?
Or Google Images? Or Wikipedia? Or...asking me?

Under the heading '19th Century' came the usual suspects: Edison, Marx, Bell...and the 1899 patent for aspirin. You'd think that a major news magazine would fact-check the structure of arguably the most popular drug in history, right? You'd be wrong.

What's missing? Well, for one, that's not even the right molecule! There's an extra methyl, and we're missing an acid proton. Furthermore, even if that structure were correct, you're missing all the charges: O should have a "+," and the COO a "minus."

Maybe that's why the "penicillin" graphic (1928) wisely depicts just a blue injection bottle.

Dear Time Magazine: We have to have a heart-to-heart. This isn't the first time you've published scientific snafus, and I know it won't be the last. I'd like to help. Hell, I'd even volunteer! If any Time editors have questions about chemical structures or terminology, please let me know, before you hit "publish" on yet another chemical mishap.

Coloring Soft Robots - "Fun" Supplemental Info?

Have you seen George Whitesides' new soft, color-changing, 3D-printable (huggable?) robots? They're out in Science right now, and Ed Yong's got a rockin' writeup over at his blog.

Source: Science | Discover | Harvard

The silicone based robots, mimics of squid, octopus, and other sea life, are pneumatically controlled - they 'move' when pumped around the lab. Colors are charged via pressurized microfluidic channels, and matched to the critter's surroundings using an algorithm. A few online videos (Harvard, and Science SI) show the robot 'dancing,' trying out its camouflage, and even glowing in the dark.

Reading through the supporting information, I had to chuckle at some of the phrasing that truly differentiates a 'Whitesides paper' from a normal chemist's jaunt. Here's some choice phrases:

"Ecoflex two-part platinum cure silicone rubber kits...purchased from Smooth-On, Inc."

"...we made aqueous solutions colored in the visible spectrum...by mixing and adjusting the relative proportions of gouache watercolor paints..."

"This chemistry is standard for commercially available glow sticks"

"Fluorescent solutions were created by dispensing approximately 2 mL of DayGlo paint...and diluting with 25 mL acetone"

Makes discussions of where you purchased your LAH and allyl bromide seem rather pedestrian, eh?

For Your Consideration...

A New, Improved 47-Step Synthesis of Shootmenowicene

Editor: We originally sent a 1600 x 1200
color abstract. Just picture a 15-member
macrolide, densely functionalized with
heterocycles, five stereocenters,
 and chelated iron.

Abstract: Shootmenowicene, a heterocycle-containing polyketide macrolide polyene siderophore, was originally isolated in 0.009% from immature sprouts of the Bungus bungus tree. We report herein a significantly shortened 47-step route to the natural product (down from 48), which we believe will allow for kilo-scale synthesis for future clinical trials.

Synthetic highlights include: extensive use of Yamamoto's "super-silyl" protecting group, a Sezen C-H arylation / macrocyclization, kilo-scale flash-vacuum pyrolysis (FVP), and enantioselective tributyltin hydride reduction. Efforts to adapt "green" chemical considerations have been made - the penultimate oxidation occurs by swirling flask in open air for three days over twenty equivalents iron oxide catalyst.

This streamlined route utilizes seventeen silica gel purifications, four alumina plugs, two resolutions: D(-)-tartaric acid and 1R(-)-10-camphorsulfonic acid (the expensive ones, sorry!), and a one-pot global HF / Hg / chromic acid deprotection protocol. Overall yield was 0.0008%, as a mixture of diastereomers (brsm).

Two medicinally active methylated analogues will be reported in due course.

Thanks to Derek for the initial inspiration, with a gentle nudge courtesy of Chemjobber.

Weekend Warrior...at Work

Chemists, do you work weekends? Should you?

Let me clarify: as a chemical professional, I know that I'll never work the "9-to-5" hours popular in the modern workforce. The reality ends up somewhere between forty-five and sixty hours per week. I also realize I have responsibilities to my employer that continue after I leave lab for the evening: 

1. Light email correspondence. 
2. Taking emergency phone calls. 
3. Reading through the literature to keep up with the "current art."

But when I say work weekends, I mean arriving at lab on Saturday and Sunday like you would on Monday-Friday: starting new reactions, taking TLCs, ordering supplies, reading drafts, everything. The Whole Nine Yards.

All work and no play make Homer
something something...

Yes, I was a graduate student once. I distinctly remember fourteen-hour shifts as de rigueur, with at least eight more hours over the weekend to keep momentum going. I worked this pace for the incentive of a terminal degree, with the promise of a brighter future where I'd at least get major holidays off. As a postdoc, your pace often intensifies, since you have limited time and resources to make a big enough splash that you'll be considered "marketable" to someone - someone who might offer you major holidays and two weeks' vacation. 

Maybe.

Well, the working world hasn't really panned out like I thought. Evening meetings occur more regularly, working lunches are standard, and now the work week bleeds into the weekend. Chores at home go unfinished. Family and friends are ignored. How's that old expression go? 

"All work and no play make Jack a dull boy."

Could this actually be counterproductive? Sure: tired workers make more mistakes, call in for more sick days, and generally don't feel as invested in company goals or culture. There's also the question of expectation - weekend work becomes an accepted part of your schedule, and employers will anticipate your future willingness to sacrifice personal time for career goals (Weekends? Nights? Holidays? Double shifts? Sleep under my desk? Sure!). 

I could tell you I was here this weekend, but...
Source: Abbi Perets

The irony mounts Monday morning, when the inevitable question comes up - "So, how was your weekend?" The person asking actually expects you to talk about things you did outside of work!

What's the solution? Companies could hire more employees or offer performance incentives, but the weak economy has subdued these approaches. Managers could sit with their chemists to identify where investments in equipment or sourcing could lighten their loads, but this assumes the capital exists to finance such ventures. No, I'd guess that, for the foreseeable future, the "weekend warrior" will continue to wage war...from work.

Coloring Book Chemistry, Part 4

Roulland, 2012

While casually strolling through the JOC ASAPs, I came across another one of those structures, sitting astride an otherwise fine synthesis of (-)-Exiguolide.

At first, I just thought it was another KCN macrolide, but then, I realized the truth: none of these authors have ever worked with him. They've colored the structure in on their own!

The 'coloring-book compound' disease appears to be spreading...

Now, I ask you, dear readers: how does this pigmentation contribute to knowledge about the molecule? After all, Fuwa, Lee, and Scheidt have all managed to construct exiguolide without reaching for the crayons or paint set; don't ask about Rao, his might be worse.

Rao, 2012

I can understand use of color to highlight a transformation, sure, or maybe to map synthons onto a structure. But does this much really help?

Do colored structures entice you to read on, or do they get under your skin, even just a little bit? Share your opinions in the comments.

Time's Terpenoids Need Chem Context

The latest issue of Time discussed drought impact on food flavoring molecules: Health & Science section, p. 26. Seeing words like sucrose, sulfur, and capsaicin in a major magazine perked up my chem "spider sense," but I balked at the description under "bitter" vegetables like dill, fennel, or carrots. The exact passage reads:

"Chock-full of terpenoids, or aromatic compounds, that become especially concentrated during drought conditions"

OK, Time, what did you mean, exactly? Context clues are key - the author wants the word "aromatic" to describe sense impact, or how these compounds taste and smell. Of course, when I think "aromatic compounds," I imagine cyclic molecules with lots of pi electrons, stabilized through conjugation.

Can't we both be right? Of course! Certain compounds fit both criteria - they have both an aromatic ring and also smell good. Then, of course, there's terpenoids that don't fit either rule. Most play to the middle: they're odiferous, but would still make Huckel cry himself to sleep.

Either way, a little context goes a long way to helping people understand the wide array of flavor compounds in their food...without causing chemistry consternation.

Update (8/9/12) - Fixed image, deleted THC, added thymol as a more representative volatile terpenoid

RIP Fleischmann, "Cold Fusion" Creator

It's not every day my Google News feed proclaims a famous chemist's passing. So it was that the AP relayed the obituary of Martin Fleischmann, one half of the Fleischmann / Pons duo that first reported table-top, room temperature energy production from an electrochemical cell, dubbed "cold fusion." 

1989: At a University of Utah press conference, Fleischmann (r)
and Pons announce their results, two weeks ahead of publication.

The Fleischmann story provides a parable for the perils of overselling early results. Ironically, Fleischmann had already made quite a career for himself: he'd been made a Royal Society Fellow years before the cold fusion controversy.

I won't go too deeply into the scientific frenzy the scientists' impromptu press conference generated (see Curious Wavefunction for a recap). But the sage Santayana paraphrase "Those who don't know history are doomed to repeat it" seems apt, given the recent GFAJ-1 / 'arsenic life' debacle. Turns out, exciting results demand replication, and this publicity can bring more attention than you augured for. 

When the press calls, you'd better have the extraordinary evidence to back up your claims.

Fake Headlines: Curiosity Lander

At about 10:31 PDT, the newest lander, Curiosity, landed on the surface of Mars. Here's a few bon mots, partially culled from Twitter and the JPL livestream (also, try the Mission home page).

Source: Xeni Jardin | iO9 | JPL

1. Ironically, Curiosity first landed in a giant Martian ocean.

2. Senior rovers Spirit and Opportunity were waiting on the surface with party snacks and a banner.

3. The very first image Curiosity took, before the grainy wheel shot, showed some little green men sitting under a black obelisk.

4. Also sighted: a blue Police Box.

5. "Seven Minutes of Terror!" roller coaster underway at Disney World.

6. Next potential rover name: Marvin.

Why, yes, I am!
Source: JPL | NASA

For more (real) Curiosity updates, stay tuned to @MarsCuriosity on Twitter.

Friday Fun - Puns in Native Tongues

Finally! For those chemists who just can't get into a scientific paper without a witty one-liner, Angewandte Chemie delivers. Derek, Excimer, and Chiral Jones noted some of the best (and worst) Angewandte abstract puns over the past 5 years. Hey, any journal that can somehow channel carbene reactions through Britney Spears deserves at least a chuckle.

Well, up to now, most of the puns have been written by the English language editors of the International Edition; regular readers realize that Angewandte publishes a German-language edition as well. Far as I can tell, looking at the 'Early View' tab, they're now translating even the puns ins Deutsch!


From the posted few, we can glimpse some method in the madness. Certain expressions are translated directly, like Goldstandard for "Gold Standard," or Elektrisierende Ergebnisse (Electrifying Results!) for "Electric Results" in English.

A few, however, must not have carried over well enough. "More than LiP service" in English becomes Ein Hauch von Rot (A Touch of Red), and "A gel for all seasons" becomes Ein Gel für alle Fälle (A gel for all cases). The strangest rewrite has to belong to this Fukuyama synthesis of Chartelline C. The reserved German tagline reads Von großen und kleinen Ringen (Of large and small rings), but the English?

"What a core-ker!"

(Must have sounded better in the pub)

Air - Periodic Refreshment

Heard about Air? It's a new malt beverage slowly permeating the Left Coast club scene. Its full brand name, "Alcohol Inspired Refresher," wants both a hyphen and a clearer concept of how an alcoholic drink can 'inspire' itself.

But, I digress...look at that cool packaging!

I'll admit, I'm a sucker for any consumer item that yokes the strangely brand-less periodic table into a marketing scheme. Look at those bold internal letters, the clean font, the stately blue rectangle. Based on previous experience, I'm guessing the atomic number of Air to be either 4 or 95; someone had better tell beryllium and americium that they'll soon be sleeping on the couch. The trademark (TM) symbol prompts another chuckle - what if Einstein, Bohr, or Seaborg could have profited from their respective elements?

Well, as they say, nothing's new under the sun: the periodic table watermark already appears on chocolate, wine, and famously at an MIT watering hole. But canned air? It's been done.

Mel Brooks at his finest.
Credit: Spaceballs | MGM