Nucleophilic Catalysis of Hydrazone Formation and Transimination: Implications for Dynamic Covalent Chemistry
Top Cited Papers
- 18 November 2006
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (49), 15602-15603
- https://doi.org/10.1021/ja067189k
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.Keywords
This publication has 10 references indexed in Scilit:
- Nucleophilic Catalysis of Oxime LigationAngewandte Chemie-International Edition, 2006
- Dynamic Combinatorial ChemistryChemical Reviews, 2006
- Scandium(III) Catalysis of Transimination Reactions. Independent and Constitutionally Coupled Reversible ProcessesJournal of the American Chemical Society, 2005
- Tethering: Fragment-Based Drug DiscoveryAnnual Review of Biophysics and Biophysical Chemistry, 2004
- Dynamic Covalent ChemistryAngewandte Chemie-International Edition, 2002
- Imine exchange inO-aryl andO-alkyl oximes as a base reaction for aqueous ‘dynamic’ combinatorial libraries. A kinetic and thermodynamic studyJournal of Physical Organic Chemistry, 1999
- Chemistry of sulfoxides and related compounds. XLII. Nucleophilic alkylidene transfer reagents. Anions of N-(p-tolylsulfonyl)sulfoximinesJournal of the American Chemical Society, 1973
- Cyanohydridoborate anion as a selective reducing agentJournal of the American Chemical Society, 1971
- The Arylation of EnaminesJournal of the American Chemical Society, 1962
- Studies on the Mechanism of Oxime and Semicarbazone Formation1Journal of the American Chemical Society, 1959