Site-selective three-component reaction for dual-functionalization of peptides.
A site-selective dual-functionalization of peptides is presented, involving readily available maleimides as well as N-hydroxylamines. The modification proceeds through a three component 1,3-dipolar cycloaddition, forming a stable product. This was exemplified by the one-pot attachment of two molecular imaging moieties to a tumor binding cyclic peptide, and was extended to the conjugation of a DOTA chelator to a 12 kDa protein.
Department of Chemistry, Faculty of Science, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg, Denmark.
Henrik K
HK
Munch
Jakob E
JE
Rasmussen
Gina
G
Popa
Jørn B
JB
Christensen
Knud J
KJ
Jensen
D001665:Binding Sites; D019811:Hydroxylamine / Q000737:chemistry; D008301:Maleimides / Q000737:chemistry; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010456:Peptides, Cyclic / Q000737:chemistry*; D011487:Protein Conformation; D013379:Substrate Specificity
D008301:Maleimides; D010456:Peptides, Cyclic; C043592:maleimide; D019811:Hydroxylamine