Beilstein Journal of Organic Chemistry (Jul 2018)

Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

  • Takao Shoji,
  • Hiroki Fukutomi,
  • Yohei Okada,
  • Kazuhiro Chiba

DOI
https://doi.org/10.3762/bjoc.14.169
Journal volume & issue
Vol. 14, no. 1
pp. 1946 – 1955

Abstract

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Artificial orthogonal bond formations such as the alkyne–azide cycloaddition have enabled selective bioconjugations under mild conditions, yet naturally occurring linkages between native functional groups would be more straightforward to elaborate bioconjugates. Herein, we describe the use of a phosphodiester bond as a versatile option to access various bioconjugates. An opposite activation strategy, involving 5’-phosphitylation of the supported oligonucleotides, has allowed several biomolecules that possess an unactivated alcohol to be directly conjugated. It should be noted that there is no need to pre-install artificial functional groups and undesired and unpredictable perturbations possibly caused by bioconjugation can be minimized.

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