[4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside.
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ABSTRACT:
SUBMITTER: Bujalska A
PROVIDER: S-EPMC9175100 | biostudies-literature | 2022 Jun
REPOSITORIES: biostudies-literature
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[4 + 2] and [2 + 4] cycloaddition reactions on single- and double-stranded DNA: a dual-reactive nucleoside.
Bujalska Anna A Basran Kaleena K Luedtke Nathan W NW
RSC chemical biology 20220505 6
Here we report dual reactivity of diene-modified duplex DNA containing 5-(1,3-butadienyl)-2'-deoxyuridine "BDdU". Normal-electron demand [4 + 2] cycloaddition proceeded upon addition of a maleimide, whereas inverse-electron demand [2 + 4] cycloaddition occurred upon addition of a tetrazine to give a novel, photoswitchable product. ...[more]
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