Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 10, Pages 6593-6604Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00583
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Funding
- Ministerio de Economia y Competitividad [CTQ2017-84779-R]
- Generalitat de Catalunya [2017SGR391]
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Oligonucleotides, peptides, and peptide nucleic acids incorporating 7-oxanorbornene as a dienophile were reacted with tetrazines linked to either a peptide, D-biotin, BODIPY, or N-acetyl-D-galactosamine. The inverse electron-demand Diels-Alder (IEDDA) cycloaddition, which was performed overnight at 37 degrees C, in all cases furnished the target conjugate in good yields. IEDDA reactions with 7-oxanorbornenes produce a lower number of stereoisomers than that of IEDDA cycloadditions with other dienophiles.
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