TY  - JOUR
A1  - Kaufmann, Janik
A1  - Müller, Patricia
A1  - Andreadou, Eleni
A1  - Heckel, Alexander
T1  - Green-Light Activatable BODIPY and Coumarin 5'-Caps for Oligonucleotide Photocaging
T2  - Chemistry – a European journal
N2  - We synthesized two green-light activatable 5’-caps for oligonucleotides based on the BODIPY and coumarin scaffold. Both bear an alkyne functionality allowing their use in numerous biological applications. They were successfully incorporated in oligonucleotides via solid-phase synthesis. Copper-catalyzed alkyne-azide cycloaddition (CuAAC) using a bisazide photo-tether gave cyclic oligonucleotides that could be relinearized by activation with green light and were shown to exhibit high stability against exonucleases. Chemical ligation as another example for bioconjugation yielded oligonucleotides with an internal strand break site. Irradiation at 530 nm or 565 nm resulted in complete photolysis of both caging groups.
KW  - photochemistry
KW  - oligonucleotides
KW  - photolabile protecting groups
KW  - green gap
KW  - photo-tethering
KW  - click chemistry
KW  - bioconjugation
Y1  - 2022
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/79097
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-790972
SN  - 1521-3765
N1  - This work was funded by the Deutsche Forschungsgemeinschaft (SFB 902). Open Access funding enabled and organized by Projekt DEAL.
VL  - 28
IS  - 36, art. e202200477
SP  - 1
EP  - 7
PB  - Wiley-VCH
CY  - Weinheim
ER  -