In Situ Formation of N-Trifluoroacetoxy Succinimide (TFA-NHS): One-Pot Formation of Succinimidyl Esters, N-Trifluoroacetyl Amino Acid Succinimidyl Esters, and N-Maleoyl Amino Acid Succinimidyl Esters
The Journal of Organic Chemistry2011Vol. 76(21), pp. 9169–9174
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Abstract
A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.
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