TY  - JOUR
A1  - Zellmann, Felix
A1  - Göbel, Michael
T1  - A trisbenzimidazole phosphoramidite building block enables high-yielding syntheses of rna-cleaving oligonucleotide conjugates
T2  - Molecules
N2  - The RNA cleaving catalyst tris(2-aminobenzimidazole) when attached to the 5’ terminus of oligonucleotides cuts complementary RNA strands in a highly site-specific manner. Conjugation was previously achieved by the acylation of an amino linker by an active ester of the catalyst. However, this procedure was low yielding and not reliable. Here, a phosphoramidite building block is described that can be coupled to oligonucleotides by manual solid phase synthesis in total yields around 85%. Based on this chemistry, we have now studied the impact of LNA (locked nucleic acids) nucleotides on the rates and the site-specificities of RNA cleaving conjugates. The highest reaction rates and the most precise cuts can be expected when the catalyst is attached to a strong 5’ closing base pair and when the oligonucleotide contains several LNA units that are equally distributed in the strand. However, when placed in the 5’ position, LNA building blocks tend to diminish the specificity of RNA cleavage.
KW  - 2-aminobenzimidazole
KW  - artificial ribonuclease
KW  - DNA-LNA mixmers
KW  - guanidine analogs
Y1  - 2020
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/54391
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-543916
SN  - 1420-3049
VL  - 25
IS  - 1842
PB  - MDPI
CY  - Basel
ER  -