Nam Tran Hoang; Thomas Kodadek
ACS Comb. Sci., 2018, 20, 2, 55-60
https://doi.org/10.1021/acscombsci.7b00151

Abstract

One-bead-one-compound (OBOC) libraries constructed by solid-phase split-and-pool synthesis are a valuable source of protein ligands. Most OBOC libraries are comprised of oligoamides, particularly peptides, peptoids and peptoid-inspired molecules. Further diversification of the chemical space covered by OBOC libraries is desirable. Towards this end, we report here the efficient proline-catalyzed asymmetric Mannich reaction between immobilized aldehydes and soluble ketones and anilines. The reaction conditions do not compromise the amplification of DNA by the PCR. Thus, this chemistry will be useful for the construction of novel DNA-encoded libraries by solid-phase synthesis.