BOP-OXy, BOP-OBt, and BOP-OAt: novel organophosphinic coupling reagents useful for solution and solid-phase peptide synthesis

J Pept Sci. 2014 Jan;20(1):1-6. doi: 10.1002/psc.2579. Epub 2013 Nov 22.

Abstract

Stand-alone coupling reagents derived from bis(2-oxo-3-oxazolidinyl)phosphorodiamidic chloride show efficient performance in solution and SPPS. In particular, the Oxyma Pure (Luxembourg Biotech., Tel Aviv, Israel) derivative shows the additional advantage of being highly soluble in DMF and even fairly soluble in CH3 CN, which can extend its use for the synthesis of complex peptides. These new stand-alone coupling reagents have the advantage of not bearing any counteranion such as PF6 or BH4 , whose presence can jeopardize the purification of final peptides prepared in solution.

Keywords: BOP-Cl; Oxyma Pure; amino acids; phosphorous reagent; solid-phase peptide synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Oxazolidinones / chemical synthesis*
  • Peptides / chemical synthesis*
  • Phosphinic Acids / chemical synthesis*
  • Solid-Phase Synthesis Techniques
  • Solubility
  • Solutions

Substances

  • Oxazolidinones
  • Peptides
  • Phosphinic Acids
  • Solutions