title: 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.
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.
authors.affiliation: ADD Organic Operations (Department 04KA, Building AP-8B) Diagnostics Division, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, Illinois 60064-6016, United States. Nicholas.Leonard@abbott.com
authors.forename: Nicholas M
authors.initials: NM
authors.lastname: Leonard
authors.forename: Jarmila
authors.initials: J
authors.lastname: Brunckova
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism; D013388:Succinimides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004952:Esters; C570522:N-trifluoroacetoxy succinimide; D013388:Succinimides