Enantiopure RNA Precursors from Nearly Racemic Starting Materials

Significance

Blackmond and colleagues report the synthesis of enantiopure RNA precursors from nearly racemic starting materials. The study draws on the recent reports of Sutherland and co-workers (Nature 2009, 459, 239; J. Am. Chem. Soc. 2010, 132, 16677), who demonstrated that pyrimidine and purine nucleotides could be synthesized from simple building blocks under prebiotically plausible conditions. Through a series of ex-periments with nearly racemic amino acids, which undergo amplification of chirality via physical processes and then act as ‘kinetic resolvers’ of gly­ceraldehyde in Sutherland’s system, Blackmond and co-workers successfully demonstrated how these RNA precursors can be obtained in enantiopure form. Proline with an enantiomeric excess as low as 1% was shown to effect this process.