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Modification of oligonucleotides via covalent attachment chemistry is a valuable tool in molecular biology and bioengineering among other fields. Multiple strategies exist for attaching reporters or enabling surface immobilization. In addition to our amino modifier phosphoramidites commonly employed for these purposes, we offer 5'-Hydrazide-modifier-6CEP1 (BA 0384) and 5'-Trityl-hydrazide-modifier CEP(BA 0385) as additional covalent attachment tools. Whereas the amino modifiers utilize active esters under basic conditions, or Schiff base formation followed by reduction, the hydrazide modification allows reaction with aldehydes under neutral to slightly acidic conditions. This reaction is fast, high yielding, and suitable for cell culture experiments. The resultant hydrazone does not require a reduction step to ensure stability. Hydrazide-containing phosphoramidites can be incorporated into oligonucleotides using standard protocols and reagents, and the trityl protecting group can be easily removed with acetic acid.
Hydrazides have been useful tools in protein and carbohydrate chemistry, and more recently in oligonucleotide bioconjugation.(1) The lack of easily available hydrazide-containing phosphoramidite building blocks has impeded more widespread use of these tools in the post-synthetic modification of oligonucleotides. In addition to our amino modifier and aminooxy phosphoramidites, we offer two hydrazide modifier phosphoramidites, BA0384 and BA0385, the former with a spacer for use with post-synthetic covalent attachment chemistry. Both products employ non-methoxy trityl (Tr) protection.
- (a) Raddatz, S.; Mueller-Ibeler, J.; Kluge, J.; Wab, L.; Burdinski, G.; Havens, J. R.; Onofrey, T. J.; Wang, D.; Schweitzer, M. Nucleic Acids Research, 2002, 30 (21) 4793-4802. (b) Antsypovich, S. I.; Oretskaya, T. S.; von Kiedrowski, G.; Rus. Chem. Bull. Int. Ed. 2005, 54, 2671-2681.
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