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  • Improved synthesis of C-terminal peptide thioesters on "safety-catch" resins using LiBr/THF.

Improved synthesis of C-terminal peptide thioesters on "safety-catch" resins using LiBr/THF.

Organic letters (2001-09-28)
R Quaderer, D Hilvert
ABSTRACT

[reaction: see text] The alkanesulfonamide "safety-catch" resin has proven useful for Fmoc-based synthesis of C-terminal peptide thioesters. We now report that the yield of isolated thioester can increase significantly when the cleavage reaction is carried out in 2 M LiBr/THF rather than DMF or THF. The largest effects are seen with problematic peptides that aggregate or form secondary structures on the resin.