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Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester.

ABSTRACT: 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.

SUBMITTER: Shoji T

PROVIDER: S-EPMC6071721 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester.

Shoji Takao T Fukutomi Hiroki H Okada Yohei Y Chiba Kazuhiro K

Beilstein journal of organic chemistry 20180727

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 ...[more]

PMID: 30112100

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