Assembling ligands in situ using bioorthogonal boronate ester synthesis

Chem Biol. 2010 Nov 24;17(11):1171-6. doi: 10.1016/j.chembiol.2010.09.008.

Abstract

Many molecules that could manipulate cellular function are not practical due to their large size and concomitant undesirable pharmocokinetic properties. Here, we describe a bioorthogonal, highly stable boronate ester (HiSBE) synthesis and use this reaction to synthesize a biologically active molecule from smaller precursors in a physiological context. The rapid rate of HiSBE synthesis suggests that it may be useful for assembling a wide variety of biologically active molecules in physiological solutions.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Dimerization
  • Esters
  • Kinetics
  • Ligands*
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Receptors, Thrombopoietin / chemistry
  • Receptors, Thrombopoietin / metabolism
  • Salicylamides / chemical synthesis
  • Salicylamides / chemistry

Substances

  • Boronic Acids
  • Esters
  • Ligands
  • Peptides
  • Receptors, Thrombopoietin
  • Salicylamides
  • salicylhydroxamic acid
  • benzeneboronic acid