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Solid‐phase synthesis of C ‐terminally modified peptides
Author(s) -
Ten Brink Hefziba T.,
Meijer Joris T.,
Geel Remon V.,
Damen Mark,
Löwik Dennis W. P. M.,
van Hest Jan C. M.
Publication year - 2006
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.780
Subject(s) - amine gas treating , moiety , chemistry , peptide , reductive amination , combinatorial chemistry , propargyl , peptide synthesis , amination , aldehyde , solid phase synthesis , alkyl , organic chemistry , amino acid , biochemistry , catalysis
In this paper, a straightforward and generic protocol is presented to label the C ‐terminus of a peptide with any desired moiety that is functionalized with a primary amine. Amine‐functional molecules included are polymers (useful for hybrid polymers), long alkyl chains (used in peptide amphiphiles and stabilization of peptides), propargyl amine and azido propyl‐amine (desirable for ‘click’ chemistry), dansyl amine (fluorescent labeling of peptides) and crown ethers (peptide switches/hybrids). In the first part of the procedure, the primary amine is attached to an aldehyde‐functional resin via reductive amination. To the secondary amine that is produced, an amino acid sequence is coupled via a standard solid‐phase peptide synthesis protocol. Since one procedure can be applied for any given amine‐functional moiety, a robust method for C ‐terminal peptide labeling is obtained. Copyright © 2006 European Peptide Society and John Wiley & Sons, Ltd.