Use of Oxyma as pH modulatory agent to be used in the prevention of base-driven side reactions and its effect on 2-chlorotrityl chloride resin

Biopolymers. 2012;98(2):89-97. doi: 10.1002/bip.21713. Epub 2011 Aug 31.

Abstract

The presence of low pKa N-hydroxylamines is beneficial in peptide chemistry as they reduce some base-mediated side reactions. Here we evaluated the applicability and buffering capacity of Ethyl 2-cyano-2-(hydroxyimino) acetate (Oxyma) in the prevention of aspartimide/piperidide formation and Pro-based overcoupling and compared it with the performance of HOBt and HOAt. In addition, the compatibility of these additives with the highly acid-labile 2-chlorotrityl chloride resin is examined.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aspartic Acid / analogs & derivatives
  • Aspartic Acid / chemistry
  • Hydrogen-Ion Concentration
  • Hydroxylamines / chemistry*
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry*
  • Pregnadienes / chemistry*
  • Trityl Compounds / chemistry*

Substances

  • Hydroxylamines
  • Peptides
  • Pregnadienes
  • Trityl Compounds
  • Aspartic Acid
  • 2-chlorotrityl chloride
  • aspartimide
  • oxyma