| Water-soluble Organocatalysts for Hydrazone and Oxime Formation. | |
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MedLine Citation:
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PMID: 23289546 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The formation of oximes and hydrazones is widely used in chemistry and biology as a molecular conjugation strategy for achieving ligation, attachment and bioconjugation. However, the relatively slow rate of reaction has hindered its utility. Here we report that simple, commercially available anthranilic acids and aminobenzoic acids act as superior catalysts for hydrazone and oxime formation, speeding the reaction considerably over the traditional aniline-catalyzed reaction at neutral pH. This efficient nucleophilic catalysis, involving catalyst-imine intermediates, allows rapid hydrazone/oxime formation even with relatively low concentrations of the two reactants. The most efficient catalysts are found to be 5-methoxyanthranilic acid and 3,5-diaminobenzoic acid; we find that they can enhance rates by factors of as much as one to two orders of magnitude over the aniline-catalyzed reaction. Evidence based on a range of differently-substituted arylamines suggests that the ortho-carboxylate group in the anthranilate catalysts serves to aid in intramolecular proton transfer during imine and hydrazone formation. |
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Authors:
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Pete Crisalli; Eric T Kool |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2013-1-4 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: - ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2013 Jan |
Date Detail:
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Created Date: 2013-1-7 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
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