title: Silyl-based alkyne-modifying linker for the preparation of C-terminal acetylene-derivatized protected peptides.
abstract: A novel linker for the synthesis of C-terminal acetylene-functionalized protected peptides is described. This SAM1 linker is applied in the manual Fmoc-based solid-phase peptide synthesis of Leu-enkephalin and in microwave-assisted automated synthesis of Maculatin 2.1, an antibacterial peptide that contains 18 amino acid residues. For the cleavage, treatment with tetramethylammonium fluoride results in protected acetylene-derivatized peptides. Alternatively, a one-pot cleavage-click procedure affords the protected 1,2,3-triazole conjugate in high yields after purification.
authors.affiliation: Inorganic Chemistry 1, Bioinorganic Chemistry, Department of Chemistry and Biochemistry, Ruhr University Bochum, Universitätsstrasse 150, D-44780 Bochum, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Strack
authors.forename: Sina
authors.initials: S
authors.lastname: Langklotz
authors.forename: Julia E
authors.initials: JE
authors.lastname: Bandow
authors.forename: Nils
authors.initials: N
authors.lastname: Metzler-Nolte
authors.forename: H Bauke
authors.initials: HB
authors.lastname: Albada
mesh_terms: D000114:Acetylene / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D004743:Enkephalin, Leucine / Q000138:chemical synthesis* / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000480:Alkynes; D010455:Peptides; D012821:Silanes; D004743:Enkephalin, Leucine; D000114:Acetylene