Enhanced Diagnostic Tools
The conjugation reaction between azides and alkynes to form 1,2,3-triazoles, as reported1 by Sharpless, was found to be so exquisitely regioselective and efficient at even the most mild conditions that Sharpless coined the term ‘Click Chemistry’ to describe it. Oligonucleotides prepared using 5’-Hexynyl Phosphoramidite are stable to standard deprotection conditions and exhibit a slightly increased retention time on RP HPLC. Azides are not compatible with oligonucleotide synthesis using phosphoramidites so a post-synthesis reaction is required. Azidobutyrate NHS Ester is used2 for azido-modification of amines at either the 3’-end or the 5’-end of an oligo and it can even be used for internal modification on an Amino-Modifier-C6 dX residue within the sequence. Specific to the 5’-terminus, 5’-Bromohexyl Phosphoramidite is added in the last cycle. This modifier can then be easily transformed into a 5’-azido group by displacement of bromide using sodium azide.3 Alkyne NHS ester allows the functionalization of an amino moiety in a variety of molecules, including DNA and RNA oligonucleotides as well as peptides or proteins. We also offer a synthesis support for labelling the 3’ terminus of oligonucleotides with an alkyne group for use in Click Chemistry. This builds upon our 1,3-diol product portfolio with the serinol backbone. A 5’-iodo-modified oligonucleotide (prepared using 5’-Iodo-dT) can be quantitatively converted to the corresponding 5’-azide.
Azidobutyrate NHS Ester
5' Bromohexyl Modifier
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