ORGANIC SYNTHESIS

Sugarcoated DNA

+ See all authors and affiliations

Science  27 Oct 2000:
Vol. 290, Issue 5492, pp. 675
DOI: 10.1126/science.290.5492.675b

Carbohydrate modifications of DNA have been observed in biological systems, and may perhaps be useful in oligonucleotide therapeutics or in the development of DNA-based materials. The synthetic modification of DNA with carbohydrate has been demonstrated, but no general route for synthesis of such hybrid molecules has existed.

Sheppard et al. have now developed such a strategy. First they prepared mono- and disaccharide phosphoramidite derivatives and then conjugated them to terminal or internal positions of oligonucleotides using solid phase synthesis. The nucleoglycoconjugate molecules form substrates for DNA-manipulating enzymes, thus enabling the synthesis of large DNA molecules with specific carbohydrate modifications. The hybrid materials combine the coding ability of DNA with the recognition ability of carbohydrates and may be used to enhance the specificity and efficiency of therapeutic oligonucleotide delivery to the cell. — JU

Angew. Chem. Int. Ed. 39, 3660 (2000).

Navigate This Article