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

Authors
Quaderer, R Hilvert, D
Citation
R. Quaderer et D. Hilvert, Improved synthesis of C-terminal peptide thioesters on "safety-catch" resins using LiBr/THF, ORG LETT, 3(20), 2001, pp. 3181-3184
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
20
Year of publication
2001
Pages
3181 - 3184
Database
ISI
SICI code
1523-7060(20011004)3:20<3181:ISOCPT>2.0.ZU;2-3
Abstract
GRAPHICS The alkanesulfonamide "safety-catch" resin has proven useful for Fmoc-based synthesis of C-terminal peptide thioesters. We now report that the yield o f isolated thioester can increase significantly when the cleavage reaction is carried out in 2 M LiBr/THF rather than DMF or THE The largest effects a re seen with problematic peptides that aggregate or form secondary structur es on the resin.