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Solid-Phase Synthesis of β-Amino Ketones Via DNA-Compatible Organocatalytic Mannich Reactions

期刊

ACS COMBINATORIAL SCIENCE
卷 20, 期 2, 页码 55-60

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acscombsci.7b00151

关键词

Mannich reaction; solid-phase synthesis; organocatalysis; one-bead-one-compound libraries; DNA-encoded libraries

资金

  1. National Institutes of Health [AG052813]

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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. Toward 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 likely be useful for the construction of novel DNA-encoded libraries by solid-phase synthesis.

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