title: 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.
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.
authors: Institute for Research in Biomedicine, Barcelona Science Park, Barcelona, Spain.
authors: Ramon
authors: R
authors: Subirós-Funosas
authors: Ayman
authors: A
authors: El-Faham
authors: Fernando
authors: F
authors: Albericio
mesh_terms: D001224:Aspartic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D006898:Hydroxylamines / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D011245:Pregnadienes / Q000737:chemistry*; D014320:Triphenylmethyl Compounds / Q000737:chemistry*
chemical_list: D006898:Hydroxylamines; D010455:Peptides; D011245:Pregnadienes; D014320:Triphenylmethyl Compounds; D001224:Aspartic Acid; C071065:2-chlorotrityl chloride; C075871:aspartimide; C045419:oxyma