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Zinc‐Catalyzed Amide Cleavage and Esterification of β‐Hydroxyethylamides
Author(s) -
Kita Yusuke,
Nishii Yuji,
Higuchi Takafumi,
Mashima Kazushi
Publication year - 2012
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.201201789
Subject(s) - catalysis , amide , bond cleavage , chemistry , cleavage (geology) , amine gas treating , serine , residue (chemistry) , peptide bond , nitrogen atom , zinc , medicinal chemistry , organic chemistry , stereochemistry , combinatorial chemistry , ring (chemistry) , materials science , enzyme , fracture (geology) , composite material
Snipping tool : Zn(OTf) 2 is an efficient catalyst for selective cleavage of amides bearing a β‐hydroxyethyl group on the nitrogen atom. The mechanism involves an N,O‐acyl rearrangement and transesterification. This new catalytic system can be applied to sequence‐specific peptide bond scission at the amine side of a serine residue. Tf=trifluoromethanesulfonyl.