Balancing Reactivity and Stability

Balancing Reactivity and Stability

Author: Saskia Neubacher

Active esters for peptide bond formation are often too reactive resulting in unwanted side reactions. N-hydroxybenzotriazoles are widely used as additives for peptide bond formation in organic solvents. N-hydroxysuccinimide esters were found to be more suitable for applications in aqueous environments in terms of shelf life and stability, despite their limited reactivity. 

Ayman El-Faham, Fernando Albericio, Institute for Research in Biomedicine, Barcelona, Spain, and colleagues, tested a variety of N-alkyl-cyanoacetamido oximes (pictured) in order to find an optimal balance between reactivity and stability. In comparison to N-hydroxysuccinimide, all tested oximes performed better, while the configuration and coupling efficiency was retained. Two additives even showed a similar performance to known ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma).

Image: © Wiley-VCH

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