A convenient one-pot synthesis of cystine-containing peptides from protected peptidyl resins using the trimethylsilyl chloride–dimethyl sulfoxide–trifluoroacetic acid system

Repurposing the Pummerer Rearrangement: Determination of Methionine Sulfoxides in Peptides

“…These harsh conditions usually covalently modify or degrade proteins. Trimethylchlorosilane (TMSCl) was an intriguing alternative to acetic anhydride or trifluoroacetic anhydride, particularly as TMSCl has been used as a cleavage and deprotection reagent in peptide synthesis and would be expected to cause minimal protein decomposition. In addition, TMSCl is often used for transient protection of sensitive groups, as it readily forms adducts with hydroxy groups or amines that are spontaneously removed during aqueous workup .…”

Evaluation of strategies for ?one-pot? deprotection, cleavage and disulfide bond formation in the preparation of cystine-containing peptides

“…This method can be quite time-consuming, due to the many steps of operation involved. Recently, one-pot synthesis strategies for peptides containing disulfide bonds which simultaneously cleave and deprotect the peptide and oxidize the cysteines have been developed [4][5][6]. Thus, cystine-containing peptides have been obtained after treatment of the protected peptidyl resins with TFA scavengers in the presence of 12 or Tl(tfa)3 [4,5].…”

“…Both 12 and Tl(tfa)3 are powerful oxidants and require careful control of the reaction conditions to prevent excessive oxidation. It has also been reported that the TMSCI-DMSO-TFA system [7,8] can be employed in such a one-pot reaction [6]. However, this method results in cleavage of S-Acm protecting groups.…”