期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 37, 页码 9394-9403出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900614
关键词
additives; calorimetry; oximes; peptide synthesis; solid-phase synthesis
资金
- CICYT [CTQ2006-03794/BQU]
- Luxembourg Bio Technologies, Ltd.
- Generalitat de Catalunya [2005SGR 00662]
- Institute for Research in Biomedicine
- Barcelona Science Park
- Ministerio de Educacion y Ciencia
- Calorimetry Platform at the Barcelona Science Park
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.
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