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Native Chemical Ligation at Valine
Author(s) -
Haase Christian,
Rohde Heike,
Seitz Oliver
Publication year - 2008
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.200801590
Subject(s) - native chemical ligation , ligation , valine , chemistry , chemical ligation , steric effects , penicillamine , yield (engineering) , peptide , peptide bond , cysteine , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , amino acid , biology , materials science , microbiology and biotechnology , enzyme , metallurgy
Peptide ligation at hydrophobic sites is possible with a ligation–desulfurization strategy in which penicillamine serves as a precursor of valine. The β,β‐dimethylcysteine peptides reacted surprisingly fast in native chemical ligation reactions. Even the sterically crowded and unpolar Leu–Val bond can be formed in high yield.