title: Orthogonal protection of peptides and peptoids for cyclization by the thiol-ene reaction and conjugation.
abstract: Cyclic peptides and peptoids were prepared using the thiol-ene Michael-type reaction. The linear precursors were provided with additional functional groups allowing for subsequent conjugation: an orthogonally protected thiol, a protected maleimide, or an alkyne. The functional group for conjugation was placed either within the cycle or in an external position. The click reactions employed for conjugation with suitably derivatized nucleoside or oligonucleotides were either cycloadditions (Diels-Alder, Cu(I)-catalyzed azide-alkyne) or the same Michael-type reaction as for cyclization.
authors.affiliation: Departament de Química Orgànica i IBUB, Facultat de Química, Universitat de Barcelona , Martí i Franquès 1-11, 08028 Barcelona, Spain.
authors.forename: Xavier
authors.initials: X
authors.lastname: Elduque
authors.forename: Enrique
authors.initials: E
authors.lastname: Pedroso
authors.forename: Anna
authors.initials: A
authors.lastname: Grandas
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D061565:Cycloaddition Reaction; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000737:chemistry*; D034444:Peptoids / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D008301:Maleimides; D009841:Oligonucleotides; D010456:Peptides, Cyclic; D034444:Peptoids; D013438:Sulfhydryl Compounds; C043592:maleimide; D003300:Copper