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DOI: 10.1055/s-0031-1289369
Enantiopure RNA Precursors from Nearly Racemic Starting Materials
J. E. Hein, E. Tse, D. G. Blackmond*
The Scripps Research Institute, La Jolla, USA
Publication History
Publication Date:
18 November 2011 (online)
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.