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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

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

Nicholas M Leonard, Jarmila Brunckova

J Org Chem. 2011 Nov 4;76(21):9169-74.

PMID: 21950593

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1234203452	5-Norbornene-2-acetic acid succinimidyl ester		1234203-45-2	Price

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