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Fmoc Solid‐Phase Synthesis of C‐Terminal Peptide Thioesters by Formation of a Backbone Pyroglutamyl Imide Moiety
Author(s) -
Tofteng A. Pernille,
Sørensen Kasper K.,
CondeFrieboes Kilian W.,
HoegJensen Thomas,
Jensen Knud J.
Publication year - 2009
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.200903710
Subject(s) - moiety , imide , peptide , amide , chemistry , peptide synthesis , peptide bond , solid phase synthesis , thioester , nucleophile , stereochemistry , combinatorial chemistry , polymer chemistry , organic chemistry , biochemistry , catalysis , enzyme
Activating an inactive bond : A new concept in synthetic peptide chemistry, backbone amide activation, proceeds through the selective conversion of a backbone amide into an imide, followed by nucleophilic acyl displacement (see scheme; Boc= tert ‐butoxycarbonyl, Pg=protecting group). This methodology represents a new approach to solid‐phase synthesis of C‐terminal peptide thioesters, and may become a general tool for the synthesis of peptide thioesters.