title: Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.
abstract: Oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate] has been tested as an additive for use in the carbodiimide approach for formation of peptide bonds. Its performance in relation to those of HOBt and HOAt, which have recently been reported to exhibit explosive properties, is reported. Oxyma displayed a remarkable capacity to inhibit racemization, together with impressive coupling efficiency in both automated and manual synthesis, superior to those of HOBt and at least comparable to those of HOAt, and surpassing the latter coupling agent in the more demanding peptide models. Stability assays showed that there was no risk of capping the resin under standard coupling conditions. Finally, calorimetry assays (DSC and ARC) showed decomposition profiles for benzotriazole-based additives that were consistent with their reported explosivities and suggested a lower risk of explosion in the case of Oxyma.
authors: Institute for Research in Biomedicine, Barcelona Science Park, Baldiri Reixac 10, 08028 Barcelona, Spain.
authors: Ramon
authors: R
authors: Subirós-Funosas
authors: Rafel
authors: R
authors: Prohens
authors: Rafael
authors: R
authors: Barbas
authors: Ayman
authors: A
authors: El-Faham
authors: Fernando
authors: F
authors: Albericio
mesh_terms: D000213:Acyl Carrier Protein / Q000737:chemistry; D000595:Amino Acid Sequence; D001372:Aza Compounds / Q000737:chemistry*; D002151:Calorimetry; D010446:Peptide Fragments / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011245:Pregnadienes / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000213:Acyl Carrier Protein; D001372:Aza Compounds; D010446:Peptide Fragments; D010455:Peptides; D011245:Pregnadienes; D014230:Triazoles; C045419:oxyma; C078985:acyl carrier protein (65-74); C012771:benzotriazole; C011852:1-hydroxybenzotriazole; C435757:1-hydroxy-7-azabenzotriazole