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: Ramon Subirós-Funosas, Rafel Prohens, Rafael Barbas, Ayman El-Faham, Fernando Albericio
• Journal: Chemistry (Weinheim an der Bergstrasse, Germany) (Chemistry) Vol. 15 Issue 37 Pg. 9394-403 (Sep 21 2009) ISSN: 1521-3765 [Electronic] Germany
• PMID: 19575348 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Acyl Carrier Protein
• Aza Compounds
• Peptide Fragments
• Peptides
• Pregnadienes
• Triazoles
• oxyma
• acyl carrier protein (65-74)
• benzotriazole
• 1-hydroxybenzotriazole
• 1-hydroxy-7-azabenzotriazole

Topics

• Acyl Carrier Protein (chemistry)
• Amino Acid Sequence
• Aza Compounds (chemistry)
• Calorimetry
• Peptide Fragments (chemistry)
• Peptides (chemical synthesis, chemistry)
• Pregnadienes (chemistry)
• Triazoles (chemistry)