An alkylsilyl-tethered, high-capacity solid support amenable to diversity-oriented synthesis for one-bead, one-stock solution chemical genetics

J Comb Chem. 2001 May-Jun;3(3):312-8. doi: 10.1021/cc000107i.

Abstract

The synthesis and use of an alkylsilyl-tethered large (500-600 microm) polystyrene resin (1) are disclosed. An optimized Suzuki coupling of bromine-functionalized polystyrene and a silicon-functionalized alkylborane generates the silicon-substituted polystyrene 1 in large scale (>100 g). Resin loading is accomplished by activation as the silyl triflate, which can accommodate even sterically encumbered secondary alcohols and phenols. Treatment with HF/pyridine for linker cleavage is mild, efficient, and amenable to an automated, large-scale distribution system. This platform delivers, minimally, 50 nmol of each small molecule derived from a diversity-oriented, split-pool synthesis on a per bead basis for use in both forward and reverse chemical genetic assays. This technology satisfies many requirements of a one bead-one stock solution approach to chemical genetics.

Publication types

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

MeSH terms

  • Alkynes / chemistry
  • Bromine / chemistry
  • Drug Delivery Systems* / instrumentation
  • Drug Delivery Systems* / methods
  • Drug Design
  • Microspheres
  • Molecular Structure
  • Polystyrenes / chemical synthesis*
  • Polystyrenes / chemistry
  • Resins, Plant / chemistry
  • Silanes / chemistry
  • Structure-Activity Relationship

Substances

  • Alkynes
  • Polystyrenes
  • Resins, Plant
  • Silanes
  • Bromine