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Oxyma: An Efficient Additive for Peptide Synthesis to Replace the Benzotriazole‐Based HOBt and HOAt with a Lower Risk of Explosion [1]
Author(s) -
SubirósFunosas Ramon,
Prohens Rafel,
Barbas Rafael,
ElFaham Ayman,
Albericio Fernando
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900614
Subject(s) - benzotriazole , carbodiimide , chemistry , racemization , peptide , explosive material , combinatorial chemistry , oxidative coupling of methane , organic chemistry , biochemistry , catalysis
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.