DNA molecules endowed with extra functional groups are very useful in a wide variety of applications including sensing, aptamer selection, and construction of materials with special properties.  Conceivably, such DNA modifications can be achieved by first incorporating a functional group handle, which allows further manipulations, on a natural nucleotide base and then conduct synthesis using either chemical methods or a DNA polymerase. In the latter case, it requires that a sidechain handle be tolerated by the DNA polymerase used. Herein we describe our work on the chemical synthesis of trans-cyclooctene modified thymidine-triphosphate and its subsequent incorporation into DNA using PCR. This modification did not affect the ability for KOD-XL DNA polymerase to recognize the modified nucleobase. After PCR, various functional groups can be incorporated into the DNA through the tetrazine-trans-cyclooctene cycloaddition click chemistry. The advantage of the proposed approach is in its simplicity and fast reaction rate. As an example, we have incorporated boronic acid into the modified DNA for various applications. Detailed will be discussed at the meeting.

Decorating DNA with boronic acids through tetrazine-<i>trans</i>-cyclooctene cycloaddition

248th National Meeting (2014)

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Decorating DNA with boronic acids through tetrazine-trans-cyclooctene cycloaddition