Cleavage and deprotection of peptides from MBHA-resin with bromotrimethylsilane

Linkers and Cleavage Strategies in Solid-Phase Organic Synthesis and Combinatorial Chemistry

“…A simple hydrolysis step is sufficient to generate the product 154.4 from the silyl intermediate 154.2 . MBHA linker was cleaved using TMSBr/thioanisole/TFA to release peptide amides …”

Evaluation of the Trifluoromethanosulfonic Acid/Trifluoroacetic Acid/Thioanisole Cleavage Procedure for Application in Solid-Phase Peptide Synthesis.

“…However, due to well-known practical and safety problems concerning use of the HF method, other acidolytic strategies have been proposed in the literature. [6][7][8] The present work alternatively evaluates the potentiality of the TFMSA/TFA/thioanisole cleavage method [9][10][11] for Boc-solid phase synthesis. Thus, the present investigation reports data found in the time-course study of TFMSA/TFA/thioanisole treatment of peptidyl-resins using solid supports routinely applied for Boc-peptide synthesis chemistry.…”

Practical, laboratory‐scale synthesis of Nin‐formyl tryptophan hydrobromide

“…At this point, we reasoned that a synthetic equivalent of HBr, a volatile acid much stronger than HCl, may offer an adequate reactivity. Correspondingly, bromotrimethylsilane, which has already found practical use in solid phase peptide chemistry [24][25][26], was freshly prepared [27] and when employed at ca. 2 M concentration and 5 : 1 molar ratio, nearly quantitative conversion of 1a into 2a was obtained [ Figure 1, Method A (see experimental part)].…”