58336-84-8Relevant academic research and scientific papers
tert-Butyl group as thiol protection in peptide synthesis
Pastuszak, Juliusz Jacek,Chimiak, Andrzej
, p. 1868 - 1873 (1981)
S-tert-Butylcysteine was obtained by a new method. A number of its N-protected derivatives and esters were synthesized. Syntheses of several peptides containing tert-butyl and acetamidomethyl or benzyl thioethers of cysteine were carried out. The tert-butyl group was removed from the thiol group of peptides by treatment with (2-nitrophenyl)sulfenyl chloride (NpsCl). The S-(2-nitrophenyl)sulfenyl derivatives so obtained were converted either into cysteine by reduction or into cystine derivatives by disproportionation. Owing to the mild deprotection conditions and the great stability of the S-tert-butyl group, the other protecting groups, particularly those of the thiols, could be easily removed from a variety of combinations.
A convenient method for regeneration of free thiol from a tert-butyl thioether
Kragulj, Elijah J.,Gustafson, Jeffery L.,Grotjahn, Douglas B.
, p. 2851 - 2854 (2008/02/13)
When dimethylmethylthiosulfonium triflate (DMTST) is added to a tert-butyl-protected thiol (RSt-Bu), the unsymmetrical disulfide RSSMe is formed. At this point the free thiol (RSH) can be obtained by the addition of trimethylphosphine and water. Most byproducts are small organic molecules that are easily removed. Georg Thieme Verlag Stuttgart.
