Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

• Main Authors: Takao Shoji, Hiroki Fukutomi, Yohei Okada, Kazuhiro Chiba
• Format: Article
• Language: English
• Published: Beilstein-Institut 2018-07-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: alkyl chain soluble supports; artificial bioconjugates; naturally occurring linkages; 5’-phosphitylation; phosphodiester bonds
• Online Access: https://doi.org/10.3762/bjoc.14.169

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.