ACS: Factoids

Yesterday, I popped along to hear Roald Hoffmann (again) talking at his own birthday symposium. Also there was author and neurologist Oliver Sacks, who is not a chemist, but when I met him this morning was wearing a very natty periodic table t-shirt. It was in colour, much better than my white-on-red version. Note to self – update wardrobe.

Back to the facts. Roald Hoffmann got a Nobel prize for some very clever theoretical chemistry and some rules that explain, and can be used to predict, why and how reactions proceed. But his first published paper was actually on the thermochemistry of cement. Fascinating.

Oliver Sacks has not only a periodic table t-shirt, but he told me that for the past 60 years has carried a periodic table in his wallet as well. I don’t think it has been the same one all that time, because it was in very good condition. And haven’t they added umpteen elements in the past 60 years.

ACS: Strictly ballroom

As much as I’ve enjoyed my forays into analytical and flavour chemistry, yesterday afternoon I had a relapse and attended the Arthur C. Cope session on organic chemistry in the cathedral-sized ballroom. Actually, the cathedral analogy doesn’t seem a bad one, as sometimes it does feel as if there’s a certain amount of worshipping going on.

I really enjoyed this session because it had an ecelectic mix of topics. Highlights for me included Kenneth Shea‘s talk on how to build polyethylene molecules from single-carbon units, in a living polymerization reaction involving ylides and diazoalkanes. In this way, he’s made some unusual polymers – such as chains with high steric congestion that can’t be prepared using traditional methods for polyolefin preparation.

I also liked Leonard MacGillivray’s presentation on solid-phase organic reactions. He co-crystallizes pairs of organic compounds to form lattices in which hydrogen-bonding aligns the molecules in a perfect orientation for reaction – specifically, photodimerization reactions between alkenes to form cyclobutanes. Because the lattice holds the molecules in very specific orientations, the stereochemistry of the process is precisely controlled.

But my favourites were Dave Macmillan and Andre Charette. Charette described his work on the preparation of chiral amines by adding organozinc reagents to N-phosphinoylimines. Now I’ve always been a bit dubious about dialkylzinc compounds, because they’re a pain to make. But Charette has thought of this, and has developed a relatively simple way to make them from zinc methoxide – so top marks for thinking of the practicalities.

MacMillan discussed his work on SOMO-activation reactions using organocatalysis. I liked the way that he gave much of the credit for this idea to his co-worker, Teresa Beeson. His group are currently developing new reactions using SOMO-activation, so expect to see enantioselective alpha-halogenation of aldehydes, vinylation reactions, and the enentioselective alkylation of cyclic ketones (which apparently requires a completely different catalyst to the one currently published).

All in all it was a top session. The only down-side was the way that people in the audience would get up and leave as soon as the speaker they were interested in had finished. I know that people have to focus on lectures in their own fields to get the most out of these meetings, but if they’d stuck around for the whole session I think they’d have found the variety of topics refreshing and stimulating.

Andy

Andrew Mitchinson (Associate editor, Nature)

ACS: In my opinion, the drug is ready

Like Catherine, I’m a bit behind on scientific posts – so here’s a quick recap of some of the talks I attended earlier in the week.

My Sunday morning started with an excellent session on malaria/anti-malarials – Solomon Nwaka from the World Health Organization’s Special Programme for Research and Training in Tropical Diseases ‘kicked off’ the session with a broad overview that really drove home why malaria is (still) such an important disease: every 30 seconds a child dies from malaria, and the disease is responsible for more that one million deaths each year. Anti-malarial drug resistance is a huge problem (and there aren’t that many new drug candidates in the pipeline), so the session focused on several academic scientists who are searching for new drug candidates. This is often done as a collaboration with Medicines for Malaria Venture, a non-profit organization created to “discover, develop and deliver new antimalarial drugs through public-private partnerships.” (For more information on public-private partnerships, click here and here).

I was only able to stay for the first half of the session, but I heard Jonathan Vennerstrom talk about synthetic peroxide anti-malarials (including this simplified analog of artemisinin) and Paul O’Neill talk about analogs of amodiaquine that were active against drug-resistant strains of malaria (click here for a recent review on 4-aminoquinoline anti-malarials).

The debate about whether or not academic scientists should try to get involved in drug discovery can get quite heated (see Derek Lowe’s take on it here; you might also be interested in this NRDD ‘Outlook’). Though I understand why some scientists think that academics should avoid this area of research, many pharmaceutical companies aren’t willing (or able) to pursue a drug discovery program that focuses on malaria or other important, yet neglected, infectious diseases that disproportionately affect developing countries. (NITD and GSK are important exceptions to this general rule…)

So my question is if many pharmaceutical companies aren’t willing/able to tackle these problems, why shouldn’t academic groups give it a try?

Joshua

Joshua Finkelstein (Senior Editor, Nature)

ACS: Avogadro’s out

Here’s a bit of gossip – Avogadro’s constant, the one that lets you work out how much is in a mole of something, is under threat from a bunch of physicists who want to see it declassified as an absolute number, and instead tied to Planck’s constant, which is altogether more complicated to explain but essentially is used in quantum mechanics to bunch things into packets, or quanta. Not very clearly explained, but I’m no physicist. Check out other definitions here and here.

The person who told me this shocking piece of news is a member of the ACS nomenclature committee. Before you all rush out and try to recalculate the number of moles in your morning coffee – don’t panic. My source tells me that on a practical day to day basis, there will be no change, although explaining moles to a tenth-grader will be more difficult if the change ever makes it through.

The paper that started it all was apparently published in the journal Metrologia, by Ian Mills, although I’m having trouble tracking down the paper.

From my brief conversation, it seems that the idea is to relate Avogadro’s number to Planck’s constant so that the number becomes a relationship between the two numbers rather than an exact number. The grandiose phrase I heard was that this would relate Avogadro’s number to the invariants of nature. What would happen in your world if suddenly you had to redefine Avogadro’s number? Anything? Nothing?

ACS: In the best possible taste

One of the great things about ACS meetings is the incredible breadth of topics that are covered. In my quest to learn about branches of chemistry that are unfamiliar to me, this morning I attended a session of the division of agricutural and food chemistry. To be precise, the lectures were all about interactions between taste and smell.

I’ve always been intrigued by flavour chemistry, and the way that the body senses chemicals and interprets them as smells and tastes. So this session was a real eye-opener. I have to say that there wasn’t much that you could really describe as chemistry – not a chemical structure in sight, in fact. But here are some interesting factoids that you might be interested in.

First off, have you ever stopped to think about why some smells seem sweet or sour, when sweet and sour are tastes? Its all to do with associations in the brain. The associations become so hard-wired that if you smell something like strawberry while you’re eating something sweet, then the taste becomes sweeter. And if you smell caramel while you’re eating something bitter, the taste seems less bitter. Perhaps most remarkably, sweet smells can even improve your tolerance to pain.

The attention you pay to a taste can also affect your enjoyment of that taste – the more you try to analyse a flavour, the less you enjoy it. Which suggests that professional wine tasters enjoy wine less than joe public. And one final thought – if all this is true, then coffee will smell different depending on whether or not you use sugar. Speaking of which, it’s time for my latest caffeine fix…

Andy

Andrew Mitchinson (Associate Editor, Nature)

ACS: So long, and thanks for all the fish

Continuing my proud tradition of not blogging in real time at ACS meetings, here are my memories of a lovely Sunday:

I went to my first ever session in the chemical toxicology division, which was a session on zebrafish organized by Peter Dedon. Knowing a bit about his background (in DNA structure/damage/etc), it was quite a surprise to find Dr. Dedon bringing this group of people together; it turns out that the simple explanation is: scientific curiousity. How delightful.

Leonard Zon gave the first talk about using zebrafish as a model system for stem cells, some of which (that prostaglandins increase the number of stem cells in bone marrow) was recently published. In some of his new work, he’s discovered a pre-cancer phenotype (a cell cluster) as well as a molecule that can reverse the clustering. As comes as no surprise, we didn’t get to see the structure of the molecule.

Patricia McGrath* gave a very informative talk about zebrafish in general, and outlined some of the ways that her company can monitor what these fish are up to for screening applications. She also gave out plastic fish, to the delight of everyone except the people who arrived too late to get them. There was also randomly a plastic fish sitting next to me – hard to know whether it was there just to get information, or perhaps to protest animal testing? In any case, it made for a good neighbor.

John Stegeman gave a great talk which highlighted the importance of carefully thinking through your biological model system: he’s found that there are significant differences in the cytochrome P450’s in zebrafish vs. humans; this is important because these Cyp450’s are the enzymes that process drugs and other foreign molecules, meaning that bioavailability and identity of any metabolites could be quite variable.

The final speaker, Jackie Lees, closed out the session by discussing cancer in fish.( Who knew??) She’s discovered an interesting correlation between cancerous cells, the presence or absence of p53, and ribosomal proteins. While their initial theory was that the ribosome was just not producing p53, it seems there may be more complicated mechanisms at work.

Overall, it was a really good session. And fish (plastic or otherwise, except for the ones with electrodes in their heads) are cute.

In other chemical toxicology news, Joanne Kotz (the senior editor at Nature Chemical Biology) has organized a session in the same division on Thursday morning, focused on understanding the full scope of what drugs do, including intended and unintended interactions. If any of you are still around that day, check it out!

Finally, I need your help: I was walking out of the convention center, and passed a room labeled ‘CHEDDUCK’. I glanced in and all I could see was people eating ice cream. Can anyone explain?

Catherine Goodman (associate editor, Nature Chemical Biology)

  • I can’t seem to find a website for either Dr. McGrath or Phylonics, the company. However, I was amused to discover that if I just searched for ‘McGrath’, this website was the first result. Coincidence? Or a convenient way to get rid of the test subjects?…

ACS: Katharine the gourmand

I have just worked out that, since saturday afternoon, all my meals have been sandwiches for one reason or another, although I almost ate a slice of cold pizza at one point, but didn’t want cheese-related nightmares so declined. I have broken the cycle now thanks to a chocolate croissant in the press room.

My mind turns to food because a major thread of this conference is the genomics of obesity. In particular I was interested to learn that human adenovirus-36, known to be the “obesity virus”, has now been shown to turn stem cells into fat cells. Magdalena Pasarica at the Pennington Biomedical Research Center and Nikhil Dhurandhar from Louisiana State university, took stem cells from the fatty tissue from a bunch of liposuction patients. Half of the batch of stem cells were exposed to Ad-36, and half not. The virus-infected stem cells developed into fat cells.

So does this mean, as long as I don’t get the virus, that I can happily eat my chocolate croissants without worry of becoming obese? Or am I missing the point?

ACS: Hello… Are there any bloggers out there?

I only have time for a quick post, but I wanted to mention a few other blogs/bloggers that are at the fall ACS meeting – most of you know that Paul and Kyle are here, but it looks like journalists from C&EN and Chemistry World are blogging from the meeting (including Carmen Drahl, who used to post at She Blinded Me with Science/who now works for C&EN…)

It also looks like Mitch (from Chemical Forums) and Eric (from Homebrew and Chemistry) are here too… Have I missed anyone? If so, please add a link to their (or your) blog in the ‘comments’ section of this post…

It sounds like some of these bloggers will be at John Harvard’s Brew House in Harvard Square tomorrow night. I’ll try to swing by for a round (and will see if I can convince any of the other NPG editors to join me) – hope to see you there…

Joshua

Joshua Finkelstein (Senior Editor, Nature)

ACS: When will I learn

Ah, the poster session. I like these things; they have allowed me to perfect that useful social skill of marching up to strangers, thrusting a hand out in the hope it will be shaken, and saying “Hi, I’m Katharine. Who are you?” Once in a while the tactic pays off and you learn something incredibly interesting.

Tonight’s session was slightly marred, not for the first time, by the realisation that members of the press had not been issued with drinks tickets. I had experienced this at the previous ACS meeting so should have anticipated it. Instead i had to charm one of the posterees into donating one of his tickets. In return i got to learn about rotaxanes that can be stacked up to make switchable liquid crystals, in a very elegant piece of chemistry. This is the first controlled, switchable liquid crystal to be made, and no surprise that the work, done by Ivan Aprahamian (thanks for the beer Ivan) comes out of the lab of Fraser Stoddart. The work was recently published.

The poster also had a molecular carousel – an incredibly complicated molecular machine with three “axes” joined at top and bottom each holding a ring that can move up and down, independently of the other rings. Hard to describe, but a carousel, where the rings represent the galloping horses, is a good analogy.

My favourite title of the evening has to be “highly absorbing superabsorbent polymers” by Thilini Mudiyanselage, from Bowling Green State University. These are hydrogels that can absorb thousands of times their own dry weight in liquid. The lightly cross-linked 3-D polymer nets expand a lot after soaking up all that water.

As usual, a huge mix of chemistry was showcased at the poster session – from a system that gets rid of bird poo, to a poster called “Girls in science” – bet you can’t guess what that was about – and try saying it without using a Muppet-esque “”https://www.islandnet.com/~pacific/spacepig.html">Pigs in Space" voice…