Document Detail


Water-soluble organocatalysts for hydrazone and oxime formation.
MedLine Citation:
PMID:  23289546     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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 1-2 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.
Authors:
Pete Crisalli; Eric T Kool
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2013-01-15
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  78     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-02-01     Completed Date:  2013-08-09     Revised Date:  2014-02-04    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1184-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Aminobenzoates / chemistry*
Catalysis
Hydrazones / chemistry*
Hydrogen-Ion Concentration
Molecular Structure
Oximes / chemistry*
Protons
Water / chemistry*
meta-Aminobenzoates / chemistry*
Grant Support
ID/Acronym/Agency:
GM067201/GM/NIGMS NIH HHS; GM068122/GM/NIGMS NIH HHS; GM072705/GM/NIGMS NIH HHS; R01 GM067201/GM/NIGMS NIH HHS; R01 GM068122/GM/NIGMS NIH HHS; R01 GM072705/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/5-methoxyanthranilic acid; 0/Aminobenzoates; 0/Hydrazones; 0/Oximes; 0/Protons; 0/meta-Aminobenzoates; 059QF0KO0R/Water; 535-87-5/3,5-diaminobenzoic acid
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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