Succinimide for NHS Esterification and Trifluoroacetylation

Trifluoroacetic acid N-succinimidyl ester (TFA-NHS) is utilized not only in the esterification of carboxy groups to form NHS esters,¹⁾ but also in the trifluoroacetylation of amines.²⁾ Furthermore, it has been reported that TFA-NHS can both protect the amino group and activate the carboxy group of aminocarboxylic acids simultaneously.³⁾ In the presence of pyridine, the reaction of an excess amount of TFA-NHS with an aminocarboxylic acid provides the N-TFA-protected aminocarboxylic acid NHS ester in a one-pot process. Such products can be used in successive condensation reactions without any purification, and is expected to be used in chemical biology research.

Related Product

S0915

Trifluoroacetic acid N-succinimidyl ester

References

• 1) Exploring Binding and Effector Functions of Natural Human Antibodies Using Synthetic Immunomodulators
  • C. E. Jakobsche, C. G. Parker, R. N. Tao, M. D. Kolesnikova, E. F. Douglass, Jr., D. A. Spiegel, ACS Chem. Biol. 2013, 8, 2404.
• 2) Reagents for the stepwise functionalization of spermine
  • R. J. Bergeron, J. S. McManis, J. Org. Chem. 1988, 53, 3108.
• 3) TFA-NHS as bifunctional protecting agent: simultaneous protection and activation of amino carboxylic acids
  • T. S. Rao, S. Nampalli, P. Sekher, S. Kumar, Tetrahedron Lett. 2002, 43, 7793.

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