948039-60-9Relevant articles and documents
The first ready-to-use benzene-based heterotrifunctional cross-linker for multiple bioconjugation
Viault, Guillaume,Dautrey, Sebastien,Maindron, Nicolas,Hardouin, Julie,Renard, Pierre-Yves,Romieu, Anthony
, p. 2693 - 2705 (2013/06/05)
The synthesis and applications of the first water-soluble benzene derivative bearing a set of three different and orthogonal bioconjugatable groups (aminooxy, azido and thiol) are described. The combined use of a 5-amino isophthalic acid scaffold and unusual acid-labile protecting groups for temporarily masking aminooxy and thiol moieties has enabled the development of a highly convergent approach towards the synthesis of such a trivalent bioconjugation platform in good yields. The potential utility of this ready-to-use cross-linking reagent for creating complex and fragile tri-component (bio)molecular systems was illustrated through (1) the rapid preparation of a three-colour FRET cascade with valuable spectral properties and (2) the luminescent/fluorescent labelling of peptides and peptide- oligonucleotide conjugates. Thus, such (bio)molecular assemblies were readily obtained via a three-step process or in a one-pot manner, both involving oxime ligation, thiol-alkylation (SN2 or Michael addition) and copper-catalysed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reactions.
