title: Fast alpha nucleophiles: structures that undergo rapid hydrazone/oxime formation at neutral pH.
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.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-5080, United States.
authors.forename: Eric T
authors.initials: ET
authors.lastname: Kool
authors.forename: Pete
authors.initials: P
authors.lastname: Crisalli
authors.forename: Ke Min
authors.initials: KM
authors.lastname: Chan
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006834:Hydrazines / Q000737:chemistry; D006835:Hydrazones / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*
chemical_list: D006834:Hydrazines; D006835:Hydrazones; D010091:Oximes