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Singh I.,NUI Maynooth | Singh I.,University of Strathclyde | Freeman C.,NUI Maynooth | Madder A.,Laboratory for Organic and Biomimetic Chemistry | And 2 more authors.
Organic and Biomolecular Chemistry | Year: 2012

Strain promoted cycloaddition is presented as a tool for RNA conjugation on the solid phase; RNA-cyclooctyne conjugates are prepared by cycloaddition to both azide (strain-promoted azide-alkyne cycloaddition, SPAAC) and nitrile oxide dipoles (strain-promoted nitrile oxide-alkyne cycloaddition, SPNOAC). The conjugation is compatible with 2′-OMe blocks and with 2′-O-TBDMS protection on the ribose moieties of the sugar. Nitrile oxide dipoles are found to be more reactive click partners than azides. The conjugation proceeds within 10 min in aqueous solvents, at room temperature without any metal catalyst and tolerates dipoles of varying steric bulk and electronic demands, including pyrenyl, coumarin and dabcyl derivatives. © 2012 The Royal Society of Chemistry. Source


Jawalekar A.M.,Radboud University Nijmegen | Op De Beeck M.,Laboratory for Organic and Biomimetic Chemistry | Van Delft F.L.,Radboud University Nijmegen | Madder A.,Laboratory for Organic and Biomimetic Chemistry
Chemical Communications | Year: 2011

2′-O-(3-(Furan-2-yl)propyl)adenosine was synthesized and evaluated for interstrand crosslink (ICL) formation in DNA duplexes. In situ oxidation of the furan moiety with NIS showed rapid crosslink formation to dA and dC, while dT and dG were inactive. © The Royal Society of Chemistry. Source


Hoogewijs K.,Laboratory for Organic and Biomimetic Chemistry | Deceuninck A.,Laboratory for Organic and Biomimetic Chemistry | Madder A.,Laboratory for Organic and Biomimetic Chemistry
Organic and Biomolecular Chemistry | Year: 2012

We herein describe the synthesis of furan containing peptides for further post-synthetic derivatisation in solution through our recently developed furan-oxidation-labeling technology. Previously, it was reported by others that during acidic cleavage of furan-modified peptides, furan moieties can suffer from degradation. We demonstrate here that this degradation is position dependent and can be fully suppressed through introduction of proximate aromatic residues. Versatile introduction of 2-furylalanine at internal, C-terminal as well as the sensitive N-terminal positions has now been proven possible. © 2012 The Royal Society of Chemistry. Source


Carrette L.L.G.,Laboratory for Organic and Biomimetic Chemistry | Verzele D.,Laboratory for Organic and Biomimetic Chemistry | Madder A.,Laboratory for Organic and Biomimetic Chemistry
Tetrahedron Letters | Year: 2010

Recently developed PEG-based resins have been shown to markedly improve the quality of the synthesis in case of the so-called 'difficult' peptide sequences. Difficult coupling reactions further require sensitive color tests for amines in the assessment of the completeness of coupling. We here describe how the use of PEG-based resins in combination with one of the more sensitive color tests in SPPS can lead to severe misinterpretation and unnecessary delays during solid phase peptide synthesis due to the presence of 'non-declared' free hydroxyl functionalities in aminomethyl-PEG-based resins. © 2010 Elsevier Ltd. All rights reserved. Source

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