期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 11, 期 16, 页码 2693-2705出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40086g
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资金
- FEDER (TRIPODE) [33883]
- CRUNCh program (CPER)
- l'Agence Nationale de la Recherche (Programme PIRIBio, ANR CLICKMASSLINK)
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 (S(N)2 or Michael addition) and copper-catalysed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reactions.
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