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

Academic Article
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Overview

authors

  • Dirksen, A.
  • Dirksen, S.
  • Hackeng, T. M.
  • Dawson, Philip

publication date

  • December 2006

journal

  • Journal of the American Chemical Society  Journal

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.

subject areas

  • Aniline Compounds
  • Catalysis
  • Hydrazones
  • Hydrogen-Ion Concentration
  • Hydrolysis
  • Kinetics
  • Temperature
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja067189k

PubMed ID

  • 17147365
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Additional Document Info

start page

  • 15602

end page

  • 15603

volume

  • 128

issue

  • 49

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