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A Cyclopropenethione-Phosphine Ligation for Rapid Biomolecule Labeling.

ABSTRACT: Cyclopropenethiones are reported as new bioorthogonal reagents. These motifs react readily with substituted phosphines to provide thiocarbonyl adducts. In some cases, the ligations are >300-fold faster than analogous reactions with bioorthogonal cyclopropenones. Dialkyl cyclopropenethiones are also stable in aqueous buffers and can be used for biomolecule labeling in vitro and in cell lysate. The rapid reactivity and biocompatibility of cyclopropenethiones suggest that they will be useful probes for cellular studies.

SUBMITTER: Row RD

PROVIDER: S-EPMC6219755 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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A Cyclopropenethione-Phosphine Ligation for Rapid Biomolecule Labeling.

Row R David RD Prescher Jennifer A JA

Organic letters 20180912 18

Cyclopropenethiones are reported as new bioorthogonal reagents. These motifs react readily with substituted phosphines to provide thiocarbonyl adducts. In some cases, the ligations are >300-fold faster than analogous reactions with bioorthogonal cyclopropenones. Dialkyl cyclopropenethiones are also stable in aqueous buffers and can be used for biomolecule labeling in vitro and in cell lysate. The rapid reactivity and biocompatibility of cyclopropenethiones suggest that they will be useful probes ...[more]

PMID: 30207474

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