Science Blackout Poetry

Inspired by Austin Kleon and the New York Times, honoring National Poetry Month.

Update (April 27): A Reddit commenter (rightly) points out to also assign credit to Tom Phillips' Humument Project...good call!

JACS 2012, 11992

JACS 2014, 5257

JACS 1993, 9293

Cutting-Edge, Nobel-Worthy Chemistry

After all the early fuss about the merits of the 2012 Chemistry Nobel Prize, I noticed this challenge, couched in an earlier Chemjobber comment thread:

"The organic chemists seem to get their hides chapped most easily when a Nobel gets awarded to a 'biologist'. It's worth asking 'what are the fundamental unanswered questions in organic chemistry?'" (Emphasis mine)

Here are three areas, broadly defined, that I believe could win the Chemistry prize next year.

Synthetic trachea
University College London, 2011

1. Whither Polymers?  Darlings of early 20th-century industry, yet they've taken a back burner lately, winning their most recent Nobel in 2000. But, what a decade! Self-healing polymers. Fluoroelastomers you can print into any shape. Synthetic organs, even, grown from biodegradable polymer scaffolds. Trouble with this prize? Picking only three winners...

2. Biochemical Assembly Lines. Yes, cue the "it's not chemistry!" complaints, but I really like work which elucidates the cellular mechanisms plants, animals, and microbes use to assemble huge, medicinally-relevant natural products. Researchers can prompt E. coli to make an antifungal compound, for instance, or yeast to make a cancer therapy. Directed evolution of these assembly proteins, or the DNA which encodes them, can lead to products with wild substitutions and unexpected properties.  Bonus: All the 'big wheels' tend to be card-carrying chemists, and work in chemistry departments. The overarching goal tends to be chemical - utilization of Nature's machinery to produce new compounds.

Usual suspects: Christopher Walsh, Chaitan Khosla, David Liu, Ben Shen.

Walsh Group, JACS 2012

3. Fundamental Catalysis. Technically, there have been a few Nobels for this fairly recently (2001, 2005, 2011). But, what a decade! Here's some currently-exploding fields:

Organocatalysis
Chiral Anion Catalysis
Gold Catalysis
New carbene ligands
Frustrated Lewis pairs
Catalytic C-H activation

Any discipline on this short list could take home a Nobel within 10 years. Admittedly, some of these are rather young, but, as Ash has pointed out, the committee has rewarded ever-shorter publication-to-prize gaps, so it's not without precedent.

Usual Suspects: Dean Toste, Melanie Sanford, Anthony Arduengo, Graham Hutchings, Douglas Stephan, David MacMillan, Benjamin List

Readers, who would you award a Chemistry Nobel?

MacMillan's Latest - Almost Autocatalysis?

There's been a veritable treasure trove of interesting reactions in JACS over the past month. One particular ASAP caught my eye today: the latest SOMO-organocatalysis reaction from the MacMillan group at Princeton University.

Back up a second, SOMO? Organocatalysis? For those readers normally not nose-first in organic journals, I'll explain a little. SOMO stands for singly-occupied molecular orbital, which means there's radical chemistry afoot! The initial intermediate in many of these reactions, an enamine, reacts with a single-electron oxidant to form a radical cation, which functions as a sort of chiral radical nucleophile...a rare duck.

Future Organocatalyst?
Pyrrolidine Power!

Organocatalysis utilizes small molecules - amines, urea derivatives, hydrogen-bond donors, or small peptides - to accelerate chemical reactions. MacMillan himself gives a good short course on the topic. Organocatalysis bridges the synthetic and biochemical worlds, adapting Nature's enzymatic tricks into new reactivity.

So, why highlight this reaction? Ever since the Soai reaction, a zinc-catalyzed alkylation first reported in 1995, chemists have been enthralled with autocatalysis, the idea that the product of a given reaction could serve as its own catalyst. In theory, you could start with a tiny bit of an (almost) racemic catalyst, and wind up with a fast, highly selective reaction.

Note the similarity between the catalyst (a pyrrolidinone) and the product (a pyrrolidine). Clip off the nosyl protecting group, and I'd believe that product capable of catalyzing its own formation. Now, I'm not usually a betting person, but I like to look skeptically for what's not mentioned. In this case, only two of the products exhibit the same 2,5 substitution as the catalysts, and the authors mention catalyst development only indirectly. 


I'll offer anyone 3:1 odds that, in the next year, an autocatalytic version of this reaction pops up.