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Readily Accessible Ambiphilic Cyclopentadienes for Bioorthogonal Labeling.

ABSTRACT: A new class of bioorthogonal reagents based on the cyclopentadiene scaffold is described. The diene 6,7,8,9-tetrachloro-1,4-dioxospiro[4,4]nona-6,8-diene (a tetrachlorocyclopentadiene ketal, TCK) is ambiphilic and self-orthogonal with remarkable stability. The diene reacts rapidly with a trans-cyclooctene and an endo-bicyclononyne, but slowly with dibenzoazacyclooctyne (DIBAC), allowing for tandem labeling studies with mutually orthogonal azides that react rapidly with DIBAC. TCK analogues are synthesized in three steps from inexpensive, commercially available starting materials.

SUBMITTER: Levandowski BJ

PROVIDER: S-EPMC6314806 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Readily Accessible Ambiphilic Cyclopentadienes for Bioorthogonal Labeling.

Levandowski Brian J BJ Gamache Raymond F RF Murphy Jennifer M JM Houk K N KN

Journal of the American Chemical Society 20180515 20

A new class of bioorthogonal reagents based on the cyclopentadiene scaffold is described. The diene 6,7,8,9-tetrachloro-1,4-dioxospiro[4,4]nona-6,8-diene (a tetrachlorocyclopentadiene ketal, TCK) is ambiphilic and self-orthogonal with remarkable stability. The diene reacts rapidly with a trans-cyclooctene and an endo-bicyclononyne, but slowly with dibenzoazacyclooctyne (DIBAC), allowing for tandem labeling studies with mutually orthogonal azides that react rapidly with DIBAC. TCK analogues are s ...[more]

PMID: 29712423

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