High-throughput photocapture approach for reaction discovery

Proc Natl Acad Sci U S A. 2020 Jun 16;117(24):13261-13266. doi: 10.1073/pnas.2003347117. Epub 2020 Jun 1.

Abstract

Modern organic reaction discovery and development relies on the rapid assessment of large arrays of hypothesis-driven experiments. The time-intensive nature of reaction analysis presents the greatest practical barrier for the execution of this iterative process that underpins the development of new bioactive agents. Toward addressing this critical bottleneck, we report herein a high-throughput analysis (HTA) method of reaction mixtures by photocapture on a 384-spot diazirine-terminated self-assembled monolayer, and self-assembled monolayers for matrix-assisted laser desorption/ionization mass spectrometry (SAMDI-MS) analysis. This analytical platform has been applied to the identification of a single-electron-promoted reductive coupling of acyl azolium species.

Keywords: azoliums; high-throughput analysis; photocapture; self-assembled monolayers.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Diazomethane / chemistry
  • High-Throughput Screening Assays / methods*
  • Oxidation-Reduction
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / methods*
  • Ultraviolet Rays

Substances

  • Benzimidazoles
  • Diazomethane