Fast Alpha Nucleophiles: Structures that Undergo Rapid
Hydrazone/Oxime Formation at Neutral pH
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Abstract
Hydrazones
and oximes are widely useful structures for conjugate
formation in chemistry and biology, but their formation can be slow
at neutral pH. Kinetics studies were performed for a range of structurally
varied hydrazines, and a surprisingly large variation in reaction
rate was observed. Structures that undergo especially rapid reactions
were identified, enabling reaction rates that rival orthogonal cycloaddition-based
conjugation chemistries