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Literature DB >> 17147365

Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry.

Anouk Dirksen¹, Sjoerd Dirksen, Tilman M Hackeng, Philip E Dawson.

Abstract

Aniline accelerates hydrazone formation and transimination through nucleophilic catalysis. To demonstrate the method, unprotected peptides are reacted and then scrambled using a hydrazone reaction under conditions relevant for biological applications. The strong enhancement in the rate of hydrazone equilibration broadens the scope of this stable imine in the field of dynamic covalent chemistry.

Entities: Chemical

Mesh：

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Year: 2006 PMID： 17147365 DOI： 10.1021/ja067189k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

92 in total

1. 4-aminophenylalanine as a biocompatible nucleophilic catalyst for hydrazone ligations at low temperature and neutral pH.

Authors: Adam R Blanden; Kamalika Mukherjee; Ozlem Dilek; Maura Loew; Susan L Bane
Journal: Bioconjug Chem Date: 2011-10-04 Impact factor: 4.774

Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry.

1. 4-aminophenylalanine as a biocompatible nucleophilic catalyst for hydrazone ligations at low temperature and neutral pH.

2. Bi-specific MHC heterodimers for characterization of cross-reactive T cells.

3. Dynamic covalent chemistry: Catalysing dynamic libraries.

4. Glycan analysis by reversible reaction to hydrazide beads and mass spectrometry.

5. Iminoboronate Formation Leads to Fast and Reversible Conjugation Chemistry of α-Nucleophiles at Neutral pH.

6. A high-throughput SAMDI-mass spectrometry assay for isocitrate dehydrogenase 1.

7. High-efficiency labeling of sialylated glycoproteins on living cells.

Review 8. Solid-phase glycan isolation for glycomics analysis.

9. Photoinduced heterodisulfide metathesis for reagent-free synthesis of polymer nanoparticles.

Review 10. Chemical probing of glycans in cells and organisms.