Fmoc-Based Synthesis of Peptide Thioacids for Azide Ligations via 2-Cyanoethyl Thioesters

R. Raz, J. Rademann – 2012

Rapid and efficient preparation of peptide thioacids from 2-cyanoethyl peptide thioesters has been accomplished. S-2-Cyanoethyl peptide thioesters were obtained cleanly without the need for purification from resin-bound tert-butyl peptide thioesters using 3-mercaptopropionitrile as a nucleophile. Elimination of the 2-cyanoethyl group proceeded rapidly (t1/2 < 8 min) under mild conditions and furnished peptide thioacids up to the size of a 16-mer. Peptide thioacids could be isolated or formed in situ and reacted smoothly with electron-deficient azides yielding an amide as the ligation product.

Titel
Fmoc-Based Synthesis of Peptide Thioacids for Azide Ligations via 2-Cyanoethyl Thioesters
Verfasser
R. Raz, J. Rademann
Datum
2012
Kennung
DOI: 10.1021/ol302247h
Quelle/n
Zitierweise
Org. Lett. 2012, 14, 5038–5041
Art
Text
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