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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.

SUBMITTER: Kool ET

PROVIDER: S-EPMC3993714 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Fast alpha nucleophiles: structures that undergo rapid hydrazone/oxime formation at neutral pH.

Kool Eric T ET Crisalli Pete P Chan Ke Min KM

Organic letters 20140221 5

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. ...[more]

PMID: 24559274

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