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In 2001, Bickel and co-workers found that L-glutamic acid can be converted to a glutamate ester using m-chloroperbenzoic acid (m-CPBA) and morpholine.[4] This is noteworthy because any self-coupling product would have introduced methionine into the N-terminal portion of the peptide. In this experiment it was found that when the acid was treated for only 5 mins at room temperature, only the glutamic ester was formed and the amine remained unreacted. If the free acid was allowed to react for 70 mins, the amine of the starting material started to couple to the acid not only in the N-terminal position but in all the other positions as well. As this experiment was done in the presence of morpholine, it was deduced that the acid was oxidized to a morpholinium salt and this salt aggregated to participate in the coupling reaction. They also demonstrated that without morpholine, the coupling reaction was less effective, which was attributed to the lack of a salt aggregate.In an interesting experiment, in 2007, Bickel and co-workers showed that L-N-acetyl-glutamic acid, L-N-acetylserine and L-N-acetylthreonine can be coupled using m-CPBA without forming a detectable amount of free amine and methionine.[4] This is the first time that it had been shown that the threonine analog, which is the second most abundant amino acid, can be coupled successfully. If the free amino acid remains unreacted, the peptide will retain purity. This experiment demonstrated that the phosphate group on amino acids is not required for coupling. As mentioned above, formylating a latter before coupling is a very effective way to inhibit the coupling reaction from forming free amine. The esterification of amino acids can give very pure peptides. The coupling reagent used is very stable and generally can be handled without worry of the well-known explosion. It forms a free radical induced by oxidation and it crosses a wide moiety range. The selectivity of the reagent is mainly determined by the nature of the coupling atom. The selectivity is generally good and gives good yields for the coupling. It has been used in many peptide synthesis.[5] d2c66b5586