Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

作者：Shoji Takao; Fukutomi Hiroki; Okada Yohei; Chiba Kazuhiro^*

来源：Beilstein Journal of Organic Chemistry, 2018, 14: 1946-1955.

DOI：10.3762/bjoc.14.169

• alkyl chain soluble supports
• artificaial bioconjugates
• naturally occurring linkages
• 5'-phosphitylation
• phosphodiester bonds

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 descnbe 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.

• 出版日期2018-7-27