Prebiotic RNA Chemistry

An article scheduled to be published in Science today describes a route to the RNA nucleotides from simple precursors found on prebiotic earth. I read about it in the NY times (also here).



There are a few things that I thought were really cool about this. One, that there were actual organic structures published in a NY times article. As far as the science goes, this excerpt from the article was striking.

"The diagram above shows, in blue, the reaction that doesn't work and, in green, the new work-around.

"Working through all possible chemical combinations for 10 years, Dr. Sutherland's team discovered a different and quite unintuitive route. Their reaction system, shown in green, combines the carbon-nitrogen chemistry that leads to the bases with the carbon-oxygen chemistry that makes the sugars. They make a half-sugar/half-base (11), add another half-sugar (12) and then a half-base to make an intermediate (13) that easily becomes ribo-cytidine phosphate."

I guess what I thought was interesting was how scientists' nomenclature and classification of the chemical 'parts' of RNA, the sugar backbone, a base, and a phosphate group, stopped them from considering alternative retrosyntheses which don't involve these pieces and prevented thinking of alternate bond disconnections.

Finally, I thought total synthesis was bad. Imagine total synthesis where the only starting materials you have to work with are simple organic compounds known to exist 1 billion years ago on earth. Maybe that's why it took this guy 10 years to make something you can probably buy from aldrich.