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Preformed Selenoesters Enable Rapid Native Chemical Ligation at Intractable Sites
Author(s) -
Durek Thomas,
Alewood Paul F.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201105512
Subject(s) - native chemical ligation , ligation , peptide , chemical ligation , computer science , chemistry , combinatorial chemistry , computational biology , information retrieval , biochemistry , cysteine , microbiology and biotechnology , biology , enzyme
Going pro : The first facile Pro–Cys ligation using a preformed prolyl selenoester is reported (see scheme; P=peptide). In a comparative study of peptide selenoesters in native chemical ligation peptide α‐selenoesters are shown to be superior acyl donors and result in rate enhancements of at least two orders of magnitude when compared to the well‐established peptide α‐thioesters. This method permits rapid chemical ligation even at previously intractable sites, such as Pro‐Cys.