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Molecules 2012, 17(12), 14174-14185; doi:10.3390/molecules171214174
Article

Synthesis of Biotin Linkers with the Activated Triple Bond Donor [p-(N-propynoylamino)toluic Acid] (PATA) for Efficient Biotinylation of Peptides and Oligonucleotides

1
,
1,2
,
3
,
4
 and
1,*
1 Department of Biosciences and Nutrition, Karolinska Institutet, Novum, SE-14183 Huddinge, Sweden 2 Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznañ, Poland 3 Clinical Research Center, Karolinska Institutet, Karolinska University Hospital Huddinge, Novum, SE-14186 Huddinge, Sweden 4 GE Healthcare Bio-Sciences AB, Björkgatan 30, SE-75184 Uppsala, Sweden
* Author to whom correspondence should be addressed.
Received: 1 November 2012 / Revised: 19 November 2012 / Accepted: 23 November 2012 / Published: 30 November 2012
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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 Hüisgen dipolar [3+2]-cycloaddition, commonly referred to as “click chemistry”. 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.
Keywords: biotin; streptavidin; click chemistry; biotin linker; oligonucleotide conjugates biotin; streptavidin; click chemistry; biotin linker; oligonucleotide conjugates
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Jezowska, M.; Romanowska, J.; Bestas, B.; Tedebark, U.; Honcharenko, M. Synthesis of Biotin Linkers with the Activated Triple Bond Donor [p-(N-propynoylamino)toluic Acid] (PATA) for Efficient Biotinylation of Peptides and Oligonucleotides. Molecules 2012, 17, 14174-14185.

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