Solid-phase synthesis of C-terminally modified peptides.
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.
Ten Brink
Hefziba T
HT
Organic Chemistry Department, IMM Institute, Radboud University Nijmegen, Toernooiveld 1, 6525 ED, Nijmegen, The Netherlands.
Meijer
Joris T
JT
Geel
Remon V
RV
Damen
Mark
M
Löwik
Dennis W P M
DW
van Hest
Jan C M
JC
D000447:Aldehydes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D000595:Amino Acid Sequence; D001671:Biochemistry / Q000379:methods*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis*; D011137:Polystyrenes / Q000737:chemistry; D012117:Resins, Synthetic / Q000737:chemistry
D000447:Aldehydes; D000588:Amines; D010455:Peptides; D011137:Polystyrenes; D012117:Resins, Synthetic