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A safety catch linker for Fmoc‐based assembly of constrained cyclic peptides
Author(s) -
Ravn Jacob,
Bourne Gregory T.,
Smythe Mark L.
Publication year - 2005
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.651
Subject(s) - linker , chemistry , cyclic peptide , peptide , cleavage (geology) , solid phase synthesis , combinatorial chemistry , amine gas treating , catechol , derivative (finance) , protecting group , peptide synthesis , stereochemistry , organic chemistry , biochemistry , alkyl , materials science , fracture (geology) , computer science , financial economics , economics , composite material , operating system
A new safety‐catch linker for Fmoc solid‐phase peptide synthesis of cyclic peptides is reported. The linear precursors were assembled on a tert ‐butyl protected catechol derivative using optimized conditions for Fmoc‐removal. After activation of the linker using TFA, neutralization of the N ‐terminal amine induced cyclization with concomitant cleavage from the resin yielding the cyclic peptides in DMF solution. Several constrained cyclic peptides were synthesized in excellent yields and purities. Copyright © 2005 European Peptide Society and John Wiley & Sons, Ltd.