title: Synthesis of biotin linkers with the activated triple bond donor [p-(N-propynoylamino)toluic acid] (PATA) for efficient biotinylation of peptides and oligonucleotides.
abstract: Biotin is an important molecule for modern biological studies including, e.g., cellular transport. Its exclusive affinity to fluorescent streptavidin/avidin proteins allows ready and specific detection. As a consequence methods for the attachment of biotin to various biological targets are of high importance, especially when they are very selective and can also proceed in water. One useful method is H&#252;isgen dipolar [3+2]-cycloaddition, commonly referred to as &#8220;click chemistry&#8221;. As we reported recently, the activated triple bond donor p-(N-propynoylamino)toluic acid (PATA) gives excellent results when used for conjugations at submicromolar concentrations. Thus, we have designed and synthesized two biotin linkers, with different lengths equipped with this activated triple bond donor and we proceeded with biotinylation of oligonucleotides and C-myc peptide both in solution and on solid support with excellent yields of conversion.
authors.affiliation: Department of Biosciences and Nutrition, Karolinska Institutet, Novum, SE-14183 Huddinge, Sweden.
authors.forename: Martina
authors.initials: M
authors.lastname: Jezowska
authors.forename: Joanna
authors.initials: J
authors.lastname: Romanowska
authors.forename: Burcu
authors.initials: B
authors.lastname: Bestas
authors.forename: Ulf
authors.initials: U
authors.lastname: Tedebark
authors.forename: Malgorzata
authors.initials: M
authors.lastname: Honcharenko
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D001710:Biotin / Q000138:chemical synthesis / Q000737:chemistry; D019921:Biotinylation; D057930:Click Chemistry; D005453:Fluorescence; D006801:Humans; D009841:Oligonucleotides / Q000737:chemistry / Q000302:isolation & purification; D010455:Peptides / Q000737:chemistry / Q000302:isolation & purification; D016271:Proto-Oncogene Proteins c-myc / Q000737:chemistry / Q000302:isolation & purification; D014867:Water / Q000737:chemistry
chemical_list: D001426:Bacterial Proteins; D001565:Benzoates; C489427:MYC protein, human; D009841:Oligonucleotides; D010455:Peptides; D016271:Proto-Oncogene Proteins c-myc; C581278:p-(N-propynoylamino)toluic acid; D014867:Water; D001710:Biotin